# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_ks
_database_code_depnum_ccdc_archive 'CCDC 1985364'
loop_
_audit_author_name
_audit_author_address
'Yasutomo Segawa'
;Nagoya University
Japan
;
_audit_update_record             
;
2020-02-20 deposited with the CCDC.	2020-04-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C50 H60 Au6 F12 N8 O2 P2 S4'
_chemical_formula_weight         2405.04

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           70
_space_group_name_H-M_alt        'F d d d'
_space_group_name_Hall           '-F 2uv 2vw'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/4, -y+1/4, z'
'x, -y+1/4, -z+1/4'
'-x+1/4, y, -z+1/4'
'x, y+1/2, z+1/2'
'-x+1/4, -y+3/4, z+1/2'
'x, -y+3/4, -z+3/4'
'-x+1/4, y+1/2, -z+3/4'
'x+1/2, y, z+1/2'
'-x+3/4, -y+1/4, z+1/2'
'x+1/2, -y+1/4, -z+3/4'
'-x+3/4, y, -z+3/4'
'x+1/2, y+1/2, z'
'-x+3/4, -y+3/4, z'
'x+1/2, -y+3/4, -z+1/4'
'-x+3/4, y+1/2, -z+1/4'
'-x, -y, -z'
'x-1/4, y-1/4, -z'
'-x, y-1/4, z-1/4'
'x-1/4, -y, z-1/4'
'-x, -y+1/2, -z+1/2'
'x-1/4, y+1/4, -z+1/2'
'-x, y+1/4, z+1/4'
'x-1/4, -y+1/2, z+1/4'
'-x+1/2, -y, -z+1/2'
'x+1/4, y-1/4, -z+1/2'
'-x+1/2, y-1/4, z+1/4'
'x+1/4, -y, z+1/4'
'-x+1/2, -y+1/2, -z'
'x+1/4, y+1/4, -z'
'-x+1/2, y+1/4, z-1/4'
'x+1/4, -y+1/2, z-1/4'

_cell_length_a                   12.360(4)
_cell_length_b                   29.522(9)
_cell_length_c                   35.0152(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     12777(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    123

_cell_measurement_reflns_used    6244

_cell_measurement_theta_min      3.2

_cell_measurement_theta_max      25.3


_exptl_crystal_description       Block

_exptl_crystal_colour            Colorless

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.501
_exptl_crystal_F_000             8864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    13.988
_shelx_estimated_absorpt_T_min   0.228
_shelx_estimated_absorpt_T_max   0.228
_exptl_absorpt_correction_type   Multi-scan

_exptl_absorpt_correction_T_min  0.446

_exptl_absorpt_correction_T_max  1.000

_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  
;
Rigaku CrystalClear-SM Expert 2.1 b29
;

_diffrn_measurement_method       'profile data from ω-scans'

_diffrn_detector_area_resol_mean 5.8140

_diffrn_reflns_number            37240
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_av_R_equivalents  0.0662
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         3.170
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2815
_reflns_number_gt                2421
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
Rigaku CrystalClear-SM Expert 2.1 b29
;
_computing_cell_refinement       
;
Rigaku CrystalClear-SM Expert 2.1 b29
;
_computing_data_reduction        
;
Rigaku CrystalClear-SM Expert 2.1 b29
;
_computing_structure_solution    SHELX-97

_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'

_computing_publication_material  
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;

_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)+(0.0233P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    ?

_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2815
_refine_ls_number_parameters     238
_refine_ls_number_restraints     83
_refine_ls_R_factor_all          0.0227
_refine_ls_R_factor_gt           0.0178
_refine_ls_wR_factor_ref         0.0420
_refine_ls_wR_factor_gt          0.0413
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Au1 Au 0.61827(2) 0.18587(2) 0.07140(2) 0.01569(6) Uani 1 1 d . . . . .
Au2 Au 0.81242(2) 0.1250 0.1250 0.01721(7) Uani 1 2 d S T P . .
S1 S 0.81637(8) 0.17852(3) 0.17214(3) 0.0192(2) Uani 1 1 d . . . . .
C1 C 0.7760(3) 0.19663(12) 0.06071(11) 0.0137(8) Uani 1 1 d . . . . .
N1 N 0.8412(2) 0.22426(10) 0.08099(9) 0.0150(7) Uani 1 1 d . . . . .
C2 C 0.9415(3) 0.22806(13) 0.06329(12) 0.0186(9) Uani 1 1 d . . . . .
C3 C 0.9366(3) 0.20102(13) 0.03040(11) 0.0177(9) Uani 1 1 d . . . . .
N2 N 0.8327(2) 0.18194(10) 0.03023(9) 0.0154(7) Uani 1 1 d . . . . .
C4 C 0.8112(3) 0.24899(13) 0.11543(11) 0.0178(9) Uani 1 1 d . . . . .
H1 H 0.7318 0.2470 0.1188 0.021 Uiso 1 1 calc R U . . .
H2 H 0.8300 0.2813 0.1119 0.021 Uiso 1 1 calc R U . . .
C5 C 0.8656(3) 0.23181(13) 0.15150(11) 0.0178(9) Uani 1 1 d . . . . .
H3 H 0.8589 0.2556 0.1712 0.021 Uiso 1 1 calc R U . . .
H4 H 0.9437 0.2282 0.1460 0.021 Uiso 1 1 calc R U . . .
C6 C 1.0319(3) 0.25419(14) 0.07239(12) 0.0231(10) Uani 1 1 d . . . . .
H5 H 1.0339 0.2731 0.0943 0.028 Uiso 1 1 calc R U . . .
C7 C 1.1179(3) 0.25096(16) 0.04771(14) 0.0316(11) Uani 1 1 d . . . . .
H6 H 1.1817 0.2678 0.0529 0.038 Uiso 1 1 calc R U . . .
C8 C 1.1143(3) 0.22354(16) 0.01511(14) 0.0331(11) Uani 1 1 d . . . . .
H7 H 1.1760 0.2223 -0.0010 0.040 Uiso 1 1 calc R U . . .
C9 C 1.0245(3) 0.19838(14) 0.00561(13) 0.0274(10) Uani 1 1 d . . . . .
H8 H 1.0226 0.1801 -0.0167 0.033 Uiso 1 1 calc R U . . .
C10 C 0.7818(3) 0.15470(14) -0.00052(11) 0.0222(10) Uani 1 1 d . . . . .
H9 H 0.7176 0.1391 0.0108 0.027 Uiso 1 1 calc R U . . .
C11 C 0.7404(4) 0.18581(15) -0.03164(13) 0.0392(12) Uani 1 1 d . . . . .
H10 H 0.6884 0.2073 -0.0207 0.059 Uiso 1 1 calc R U . . .
H11 H 0.7049 0.1678 -0.0515 0.059 Uiso 1 1 calc R U . . .
H12 H 0.8012 0.2025 -0.0428 0.059 Uiso 1 1 calc R U . . .
C12 C 0.8563(4) 0.11810(15) -0.01620(14) 0.0328(11) Uani 1 1 d . . . . .
H13 H 0.9105 0.1319 -0.0330 0.049 Uiso 1 1 calc R U . . .
H14 H 0.8136 0.0961 -0.0307 0.049 Uiso 1 1 calc R U . . .
H15 H 0.8927 0.1027 0.0050 0.049 Uiso 1 1 calc R U . . .
P1 P 0.8750 0.3750 0.15482(4) 0.0223(3) Uani 1 2 d DS T P . .
F1 F 0.8750 0.3750 0.10973(17) 0.035(3) Uani 0.5 2 d DS TU P A 1
F2 F 0.8750 0.3750 0.20076(17) 0.044(3) Uani 0.5 2 d DS TU P A 1
F3 F 0.9550(5) 0.3322(2) 0.15569(19) 0.044(3) Uani 0.5 1 d D . P A 1
F4 F 0.77228(18) 0.34201(8) 0.15504(7) 0.0319(6) Uani 1 1 d D . . . .
F5 F 0.9465(7) 0.3369(3) 0.1339(3) 0.030(4) Uani 0.25 1 d D . P A -2
F6 F 0.9147(7) 0.3544(3) 0.1952(2) 0.033(4) Uani 0.25 1 d D U P A -2
F7 F 0.8421(9) 0.3949(3) 0.1142(2) 0.031(4) Uani 0.25 1 d D U P A -2
F8 F 0.8095(10) 0.4131(3) 0.1764(3) 0.037(4) Uani 0.25 1 d D U P A -2
C13 C 0.1250 0.1250 0.1250 0.143(6) Uani 1 4 d DS TU P . .
O1 O 0.1250 0.1250 0.0869(2) 0.193(5) Uani 1 2 d DS TU P B .
C14 C 0.111(3) 0.1705(7) 0.1449(9) 0.115(7) Uani 0.25 1 d D U P B -1


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Au1 C1 2.010(4) . ?
Au1 S1 2.3036(12) 4_655 ?
Au2 S1 2.2855(11) . ?
Au2 S1 2.2855(11) 3 ?
S1 C5 1.835(4) . ?
S1 Au1 2.3036(12) 4_655 ?
C1 N1 1.348(5) . ?
C1 N2 1.349(5) . ?
N1 C2 1.391(5) . ?
N1 C4 1.458(5) . ?
C2 C6 1.395(5) . ?
C2 C3 1.403(6) . ?
C3 C9 1.393(5) . ?
C3 N2 1.401(5) . ?
N2 C10 1.484(5) . ?
C4 C5 1.518(5) . ?
C4 H1 0.9900 . ?
C4 H2 0.9900 . ?
C5 H3 0.9900 . ?
C5 H4 0.9900 . ?
C6 C7 1.373(6) . ?
C6 H5 0.9500 . ?
C7 C8 1.400(7) . ?
C7 H6 0.9500 . ?
C8 C9 1.377(6) . ?
C8 H7 0.9500 . ?
C9 H8 0.9500 . ?
C10 C11 1.514(6) . ?
C10 C12 1.522(6) . ?
C10 H9 1.0000 . ?
C11 H10 0.9800 . ?
C11 H11 0.9800 . ?
C11 H12 0.9800 . ?
C12 H13 0.9800 . ?
C12 H14 0.9800 . ?
C12 H15 0.9800 . ?
P1 F8 1.579(7) . ?
P1 F8 1.579(7) 14_655 ?
P1 F1 1.579(6) . ?
P1 F7 1.592(7) 14_655 ?
P1 F7 1.592(7) . ?
P1 F4 1.600(2) . ?
P1 F4 1.600(2) 14_655 ?
P1 F3 1.603(5) 14_655 ?
P1 F3 1.603(5) . ?
P1 F5 1.607(7) . ?
P1 F2 1.608(6) . ?
P1 F6 1.615(7) . ?
C13 O1 1.335(8) 3 ?
C13 O1 1.335(8) . ?
C13 C14 1.523(10) . ?

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 173.66(11) . 4_655 ?
S1 Au2 S1 177.55(5) . 3 ?
C5 S1 Au2 108.38(13) . . ?
C5 S1 Au1 106.66(12) . 4_655 ?
Au2 S1 Au1 96.60(4) . 4_655 ?
N1 C1 N2 107.5(3) . . ?
N1 C1 Au1 125.2(3) . . ?
N2 C1 Au1 126.9(3) . . ?
C1 N1 C2 110.3(3) . . ?
C1 N1 C4 125.9(3) . . ?
C2 N1 C4 123.7(3) . . ?
N1 C2 C6 131.1(4) . . ?
N1 C2 C3 106.3(3) . . ?
C6 C2 C3 122.5(4) . . ?
C9 C3 N2 133.6(4) . . ?
C9 C3 C2 120.6(4) . . ?
N2 C3 C2 105.8(3) . . ?
C1 N2 C3 110.1(3) . . ?
C1 N2 C10 121.9(3) . . ?
C3 N2 C10 127.5(3) . . ?
N1 C4 C5 114.1(3) . . ?
N1 C4 H1 108.7 . . ?
C5 C4 H1 108.7 . . ?
N1 C4 H2 108.7 . . ?
C5 C4 H2 108.7 . . ?
H1 C4 H2 107.6 . . ?
C4 C5 S1 117.8(3) . . ?
C4 C5 H3 107.8 . . ?
S1 C5 H3 107.8 . . ?
C4 C5 H4 107.8 . . ?
S1 C5 H4 107.8 . . ?
H3 C5 H4 107.2 . . ?
C7 C6 C2 116.0(4) . . ?
C7 C6 H5 122.0 . . ?
C2 C6 H5 122.0 . . ?
C6 C7 C8 121.9(4) . . ?
C6 C7 H6 119.0 . . ?
C8 C7 H6 119.0 . . ?
C9 C8 C7 122.3(4) . . ?
C9 C8 H7 118.8 . . ?
C7 C8 H7 118.8 . . ?
C8 C9 C3 116.6(4) . . ?
C8 C9 H8 121.7 . . ?
C3 C9 H8 121.7 . . ?
N2 C10 C11 109.7(3) . . ?
N2 C10 C12 113.0(3) . . ?
C11 C10 C12 112.1(4) . . ?
N2 C10 H9 107.3 . . ?
C11 C10 H9 107.3 . . ?
C12 C10 H9 107.3 . . ?
C10 C11 H10 109.5 . . ?
C10 C11 H11 109.5 . . ?
H10 C11 H11 109.5 . . ?
C10 C11 H12 109.5 . . ?
H10 C11 H12 109.5 . . ?
H11 C11 H12 109.5 . . ?
C10 C12 H13 109.5 . . ?
C10 C12 H14 109.5 . . ?
H13 C12 H14 109.5 . . ?
C10 C12 H15 109.5 . . ?
H13 C12 H15 109.5 . . ?
H14 C12 H15 109.5 . . ?
F8 P1 F8 122.8(7) . 14_655 ?
F8 P1 F7 145.3(6) . 14_655 ?
F8 P1 F7 92.0(4) 14_655 14_655 ?
F8 P1 F7 92.0(4) . . ?
F8 P1 F7 145.3(6) 14_655 . ?
F7 P1 F7 53.3(7) 14_655 . ?
F8 P1 F4 91.4(5) . . ?
F8 P1 F4 88.3(5) 14_655 . ?
F1 P1 F4 90.28(10) . . ?
F7 P1 F4 89.0(4) 14_655 . ?
F7 P1 F4 91.5(4) . . ?
F8 P1 F4 88.3(5) . 14_655 ?
F8 P1 F4 91.4(5) 14_655 14_655 ?
F1 P1 F4 90.28(10) . 14_655 ?
F7 P1 F4 91.5(4) 14_655 14_655 ?
F7 P1 F4 89.0(4) . 14_655 ?
F4 P1 F4 179.4(2) . 14_655 ?
F1 P1 F3 91.1(2) . 14_655 ?
F4 P1 F3 89.4(3) . 14_655 ?
F4 P1 F3 90.6(3) 14_655 14_655 ?
F1 P1 F3 91.1(2) . . ?
F4 P1 F3 90.6(3) . . ?
F4 P1 F3 89.4(3) 14_655 . ?
F3 P1 F3 177.8(5) 14_655 . ?
F8 P1 F5 177.3(6) . . ?
F8 P1 F5 55.8(5) 14_655 . ?
F7 P1 F5 36.3(5) 14_655 . ?
F7 P1 F5 89.5(5) . . ?
F4 P1 F5 90.7(4) . . ?
F4 P1 F5 89.5(4) 14_655 . ?
F1 P1 F2 180.0 . . ?
F4 P1 F2 89.72(10) . . ?
F4 P1 F2 89.72(10) 14_655 . ?
F3 P1 F2 88.9(2) 14_655 . ?
F3 P1 F2 88.9(2) . . ?
F8 P1 F6 90.3(5) . . ?
F8 P1 F6 32.5(5) 14_655 . ?
F7 P1 F6 124.4(5) 14_655 . ?
F7 P1 F6 177.0(5) . . ?
F4 P1 F6 90.4(4) . . ?
F4 P1 F6 89.1(4) 14_655 . ?
F5 P1 F6 88.1(4) . . ?
O1 C13 O1 180.0 3 . ?
O1 C13 C14 62.8(14) 3 . ?
O1 C13 C14 117.2(14) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C1 N1 C2 0.6(4) . . . . ?
Au1 C1 N1 C2 -172.9(3) . . . . ?
N2 C1 N1 C4 177.5(3) . . . . ?
Au1 C1 N1 C4 4.0(5) . . . . ?
C1 N1 C2 C6 176.4(4) . . . . ?
C4 N1 C2 C6 -0.6(6) . . . . ?
C1 N1 C2 C3 -0.1(4) . . . . ?
C4 N1 C2 C3 -177.1(3) . . . . ?
N1 C2 C3 C9 178.4(4) . . . . ?
C6 C2 C3 C9 1.6(6) . . . . ?
N1 C2 C3 N2 -0.4(4) . . . . ?
C6 C2 C3 N2 -177.3(4) . . . . ?
N1 C1 N2 C3 -0.9(4) . . . . ?
Au1 C1 N2 C3 172.5(3) . . . . ?
N1 C1 N2 C10 -173.3(3) . . . . ?
Au1 C1 N2 C10 0.1(5) . . . . ?
C9 C3 N2 C1 -177.8(4) . . . . ?
C2 C3 N2 C1 0.9(4) . . . . ?
C9 C3 N2 C10 -6.0(7) . . . . ?
C2 C3 N2 C10 172.7(3) . . . . ?
C1 N1 C4 C5 110.7(4) . . . . ?
C2 N1 C4 C5 -72.8(4) . . . . ?
N1 C4 C5 S1 -74.9(4) . . . . ?
Au2 S1 C5 C4 51.1(3) . . . . ?
Au1 S1 C5 C4 -51.9(3) 4_655 . . . ?
N1 C2 C6 C7 -177.8(4) . . . . ?
C3 C2 C6 C7 -1.8(6) . . . . ?
C2 C6 C7 C8 0.8(6) . . . . ?
C6 C7 C8 C9 0.4(7) . . . . ?
C7 C8 C9 C3 -0.7(7) . . . . ?
N2 C3 C9 C8 178.3(4) . . . . ?
C2 C3 C9 C8 -0.3(6) . . . . ?
C1 N2 C10 C11 91.5(4) . . . . ?
C3 N2 C10 C11 -79.5(5) . . . . ?
C1 N2 C10 C12 -142.7(4) . . . . ?
C3 N2 C10 C12 46.3(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C4 H2 F4 0.99 2.45 3.114(4) 124.1 .
C4 H2 F5 0.99 2.32 3.155(12) 142.0 .
C4 H2 F7 0.99 2.38 3.353(11) 166.4 14_655
C5 H3 F3 0.99 2.61 3.167(8) 115.6 .
C5 H3 F8 0.99 2.61 3.353(11) 132.1 14_655
C6 H5 F5 0.95 2.58 3.424(9) 148.7 .
C9 H8 F2 0.95 2.36 3.151(6) 140.9 19_755
C9 H8 F6 0.95 2.43 3.147(11) 132.2 32
C11 H11 F1 0.98 2.59 3.568(6) 173.4 29_655
C12 H13 F6 0.98 2.43 3.163(9) 131.0 19_755
C12 H15 S1 0.98 2.87 3.603(5) 132.1 3

_refine_diff_density_max         0.907
_refine_diff_density_min         -1.005
_refine_diff_density_rms         0.129



_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'F d d d :2'
_diffrn_radiation_source         ?
_diffrn_radiation_monochromator  Confocal
_chemical_absolute_configuration ?
####################################################################### 
# 
# 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_shelxt_a
_database_code_depnum_ccdc_archive 'CCDC 1985367'
loop_
_audit_author_name
_audit_author_address
'Alex J. Veinot'
;Queens University
Canada
;
_audit_update_record             
;
2020-02-20 deposited with the CCDC.	2020-04-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H18 Au Br N2 O S'
_chemical_formula_weight         539.24

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.2685(3)
_cell_length_b                   9.2937(3)
_cell_length_c                   10.4915(3)
_cell_angle_alpha                66.9380(10)
_cell_angle_beta                 78.8370(10)
_cell_angle_gamma                79.3620(10)
_cell_volume                     809.82(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    9758
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      30.53

_exptl_crystal_description       plate-like
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.211
_exptl_crystal_F_000             508
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.151
_exptl_crystal_size_mid          0.122
_exptl_crystal_size_min          0.102
_exptl_absorpt_coefficient_mu    11.676
_shelx_estimated_absorpt_T_min   0.272
_shelx_estimated_absorpt_T_max   0.382
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4532
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'SADABS v2016/2 (Apex3, Bruker AXS)'
_exptl_absorpt_special_details   
;The value for wR₂(int) was 0.1055 before and 0.0589
 after correction. 
 The ratio of minimum to maximum transmission is 0.6074.
;

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   
;high brilliance Incoatec I\ms microfocus tube
;
_diffrn_radiation_monochromator  'HELIOS multilayer mirror optics'
_diffrn_measurement_device_type  'Bruker AXS D8 Venture Duo'
_diffrn_detector                 
;Bruker AXS PHOTON II Charge-Integrating Pixel Array Detector (CPAD)
;
_diffrn_measurement_method       'shutterless rotation images,φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            43744
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.887
_diffrn_reflns_theta_max         30.539
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4943
_reflns_number_gt                4636
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;APEX3 software package v2018.7-2(Bruker AXS).
;
_computing_cell_refinement       
;Saint V8.38A and SADABS V2016/2 (Apex3 v2018.7-2; Bruker AXS).
 Ref. for SADABS: Krause, L.; Herbst-Irmer, R.; Sheldrick G.M.; 
 Stalke D., J. Appl. Cryst., 48 (2015), 3-10.
;
_computing_data_reduction        
;Saint V8.38A and SADABS V2016/2 (Apex3 v2018.7-2; Bruker AXS).
 Ref. for SADABS: Krause, L.; Herbst-Irmer, R.; Sheldrick G.M.; 
 Stalke D., J. Appl. Cryst., 48 (2015), 3-10. 
;
_computing_structure_solution    
; SHELXT-2014/5 (Sheldrick, 2014). G. M. Sheldrick, Acta Cryst. 2015, A71,
  3-8.
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0230P)²+0.7809P] 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         4943
_refine_ls_number_parameters     184
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0215
_refine_ls_R_factor_gt           0.0193
_refine_ls_wR_factor_ref         0.0497
_refine_ls_wR_factor_gt          0.0488
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_restrained_S_all      1.107
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Au1 Au 0.63890(2) 0.38282(2) 0.10123(2) 0.02187(4) Uani 1 1 d . . . . .
Br1 Br 0.74099(3) 0.19446(4) -0.00626(3) 0.03130(6) Uani 1 1 d . . . . .
S1 S 0.10703(8) 0.24339(9) 0.40960(8) 0.03048(14) Uani 1 1 d . . . . .
O1 O 0.1116(3) 0.3383(3) 0.6137(2) 0.0399(5) Uani 1 1 d . . . . .
N1 N 0.4441(2) 0.5114(3) 0.3019(2) 0.0210(4) Uani 1 1 d . . . . .
N2 N 0.6123(2) 0.6662(3) 0.1831(2) 0.0219(4) Uani 1 1 d . . . . .
C1 C 0.5615(3) 0.5320(3) 0.1999(3) 0.0207(4) Uani 1 1 d . . . . .
C2 C 0.4184(3) 0.6333(3) 0.3515(3) 0.0218(5) Uani 1 1 d . . . . .
C3 C 0.3150(3) 0.6623(4) 0.4562(3) 0.0271(5) Uani 1 1 d . . . . .
H3 H 0.2445 0.5918 0.5106 0.032 Uiso 1 1 calc R U . . .
C4 C 0.3198(3) 0.7995(4) 0.4775(3) 0.0299(6) Uani 1 1 d . . . . .
H4 H 0.2517 0.8232 0.5489 0.036 Uiso 1 1 calc R U . . .
C5 C 0.4227(3) 0.9033(4) 0.3963(3) 0.0293(6) Uani 1 1 d . . . . .
H5 H 0.4205 0.9977 0.4121 0.035 Uiso 1 1 calc R U . . .
C6 C 0.5279(3) 0.8735(3) 0.2935(3) 0.0259(5) Uani 1 1 d . . . . .
H6 H 0.5988 0.9438 0.2396 0.031 Uiso 1 1 calc R U . . .
C7 C 0.5242(3) 0.7346(3) 0.2733(3) 0.0213(5) Uani 1 1 d . . . . .
C8 C 0.3614(3) 0.3758(3) 0.3591(3) 0.0244(5) Uani 1 1 d . . . . .
H8A H 0.3578 0.3312 0.4621 0.029 Uiso 1 1 calc R U . . .
H8B H 0.4145 0.2940 0.3229 0.029 Uiso 1 1 calc R U . . .
C9 C 0.2036(3) 0.4159(3) 0.3229(3) 0.0262(5) Uani 1 1 d . . . . .
H9A H 0.2058 0.4517 0.2205 0.031 Uiso 1 1 calc R U . . .
H9B H 0.1512 0.5023 0.3534 0.031 Uiso 1 1 calc R U . . .
C10 C 0.0793(3) 0.2363(4) 0.5844(3) 0.0295(6) Uani 1 1 d . . . . .
C11 C 0.0143(4) 0.0921(4) 0.6901(4) 0.0400(7) Uani 1 1 d . . . . .
H11A H -0.0308 0.0434 0.6423 0.060 Uiso 1 1 calc R U . . .
H11B H -0.0614 0.1221 0.7575 0.060 Uiso 1 1 calc R U . . .
H11C H 0.0928 0.0167 0.7394 0.060 Uiso 1 1 calc R U . . .
C12 C 0.7387(3) 0.7386(3) 0.0820(3) 0.0265(5) Uani 1 1 d . . . . .
H12 H 0.7625 0.8212 0.1108 0.032 Uiso 1 1 calc R U . . .
C13 C 0.8763(3) 0.6214(5) 0.0867(4) 0.0402(8) Uani 1 1 d . . . . .
H13A H 0.8644 0.5501 0.0421 0.060 Uiso 1 1 calc R U . . .
H13B H 0.8916 0.5603 0.1842 0.060 Uiso 1 1 calc R U . . .
H13C H 0.9622 0.6778 0.0369 0.060 Uiso 1 1 calc R U . . .
C14 C 0.6923(4) 0.8217(5) -0.0622(3) 0.0414(8) Uani 1 1 d . . . . .
H14A H 0.7731 0.8773 -0.1268 0.062 Uiso 1 1 calc R U . . .
H14B H 0.6043 0.8976 -0.0585 0.062 Uiso 1 1 calc R U . . .
H14C H 0.6692 0.7442 -0.0948 0.062 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Au1 C1 1.994(3) . ?
Au1 Br1 2.3986(3) . ?
S1 C10 1.779(3) . ?
S1 C9 1.809(3) . ?
O1 C10 1.205(4) . ?
N1 C1 1.354(3) . ?
N1 C2 1.387(3) . ?
N1 C8 1.456(3) . ?
N2 C1 1.349(3) . ?
N2 C7 1.396(3) . ?
N2 C12 1.484(3) . ?
C2 C3 1.388(4) . ?
C2 C7 1.395(4) . ?
C3 C4 1.388(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.396(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.395(4) . ?
C6 H6 0.9500 . ?
C8 C9 1.524(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.505(4) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.511(4) . ?
C12 C14 1.512(4) . ?
C12 H12 1.0000 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Au1 Br1 176.54(7) . . ?
C10 S1 C9 99.89(14) . . ?
C1 N1 C2 110.5(2) . . ?
C1 N1 C8 125.3(2) . . ?
C2 N1 C8 124.1(2) . . ?
C1 N2 C7 109.9(2) . . ?
C1 N2 C12 127.0(2) . . ?
C7 N2 C12 123.1(2) . . ?
N2 C1 N1 107.0(2) . . ?
N2 C1 Au1 128.99(19) . . ?
N1 C1 Au1 123.96(19) . . ?
N1 C2 C3 132.0(3) . . ?
N1 C2 C7 106.0(2) . . ?
C3 C2 C7 122.0(2) . . ?
C4 C3 C2 116.6(3) . . ?
C4 C3 H3 121.7 . . ?
C2 C3 H3 121.7 . . ?
C3 C4 C5 121.4(3) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C6 C5 C4 122.3(3) . . ?
C6 C5 H5 118.9 . . ?
C4 C5 H5 118.9 . . ?
C5 C6 C7 116.3(3) . . ?
C5 C6 H6 121.8 . . ?
C7 C6 H6 121.8 . . ?
C2 C7 C6 121.4(2) . . ?
C2 C7 N2 106.4(2) . . ?
C6 C7 N2 132.1(3) . . ?
N1 C8 C9 113.1(2) . . ?
N1 C8 H8A 109.0 . . ?
C9 C8 H8A 109.0 . . ?
N1 C8 H8B 109.0 . . ?
C9 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C8 C9 S1 109.45(19) . . ?
C8 C9 H9A 109.8 . . ?
S1 C9 H9A 109.8 . . ?
C8 C9 H9B 109.8 . . ?
S1 C9 H9B 109.8 . . ?
H9A C9 H9B 108.2 . . ?
O1 C10 C11 123.9(3) . . ?
O1 C10 S1 122.1(2) . . ?
C11 C10 S1 114.0(2) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 C13 112.2(2) . . ?
N2 C12 C14 109.8(2) . . ?
C13 C12 C14 113.6(3) . . ?
N2 C12 H12 107.0 . . ?
C13 C12 H12 107.0 . . ?
C14 C12 H12 107.0 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

_refine_diff_density_max         0.984
_refine_diff_density_min         -1.543
_refine_diff_density_rms         0.146



