# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_c507
_database_code_depnum_ccdc_archive 'CCDC 2234522'
loop_
_audit_author_name
_audit_author_address
'M. Concepcion Gimeno'
;Instituto de Sintesis Quimica y Catalisis Homogenea
Spain
;
_audit_update_record             
;
2023-01-05 deposited with the CCDC.	2023-02-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H10 N2 S'
_chemical_formula_weight         190.26

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'

_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                   8.4085(4)
_cell_length_b                   11.4813(5)
_cell_length_c                   20.4931(7)
_cell_angle_alpha                105.562(4)
_cell_angle_beta                 100.603(3)
_cell_angle_gamma                90.042(4)
_cell_volume                     1870.73(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6167
_cell_measurement_theta_min      4.3330
_cell_measurement_theta_max      28.5180

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_F_000             800
_exptl_transmission_factor_min   0.85673
_exptl_transmission_factor_max   1.00000
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.296
_shelx_estimated_absorpt_T_min   0.886
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.85673
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω rotations'
_diffrn_detector_area_resol_mean 16.0655
_diffrn_reflns_number            21306
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_av_R_equivalents  0.0329
_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       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         4.149
_diffrn_reflns_theta_max         28.770
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.867
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.867
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.867
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             8443
_reflns_number_gt                6594
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0336P)²+0.7107P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8443
_refine_ls_number_parameters     601
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.0889
_refine_ls_wR_factor_gt          0.0810
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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
S1 S 1.18850(5) 0.88213(4) 0.12191(2) 0.02354(11) Uani 1 1 d . . . . .
S2 S 0.71429(5) 0.73141(5) 1.10233(3) 0.02912(12) Uani 1 1 d . . . . .
S3 S 0.58622(5) 0.11276(4) 0.37646(2) 0.02417(11) Uani 1 1 d . . . . .
S4 S 1.12662(5) 0.27030(4) 0.39806(2) 0.02396(11) Uani 1 1 d . . . . .
N1 N 0.91568(16) 0.89524(13) 0.03767(7) 0.0191(3) Uani 1 1 d . . . . .
N2 N 1.07533(17) 0.72940(14) 0.00005(7) 0.0206(3) Uani 1 1 d . . . . .
N3 N 0.41778(16) 0.67131(13) 1.03100(7) 0.0215(3) Uani 1 1 d . . . . .
N4 N 0.57246(17) 0.80709(14) 0.99547(7) 0.0195(3) Uani 1 1 d . . . . .
N5 N 0.38675(16) 0.10439(13) 0.46058(7) 0.0199(3) Uani 1 1 d . . . . .
N8 N 1.08023(17) 0.19459(13) 0.50486(7) 0.0187(3) Uani 1 1 d . . . . .
N6 N 0.58020(17) 0.27067(14) 0.49636(7) 0.0200(3) Uani 1 1 d . . . . .
N7 N 0.89458(16) 0.33072(14) 0.46952(7) 0.0207(3) Uani 1 1 d . . . . .
C1 C 1.04081(19) 0.83311(16) 0.04421(8) 0.0177(3) Uani 1 1 d . . . . .
C2 C 0.9213(2) 1.00148(17) 0.09665(9) 0.0222(4) Uani 1 1 d . . . . .
C3 C 1.0704(2) 1.00410(16) 0.15185(9) 0.0217(4) Uani 1 1 d . . . . .
C4 C 1.1088(3) 1.0840(2) 0.21272(10) 0.0334(5) Uani 1 1 d . . . . .
C5 C 0.97727(19) 0.66029(16) -0.06181(8) 0.0182(3) Uani 1 1 d . . . . .
C6 C 1.0103(2) 0.53883(16) -0.08478(9) 0.0209(4) Uani 1 1 d . . . . .
H6 H 1.094428 0.505792 -0.058595 0.025 Uiso 1 1 calc R U . . .
C7 C 0.9208(2) 0.46623(18) -0.14563(9) 0.0225(4) Uani 1 1 d . . . . .
C8 C 0.7967(2) 0.51352(17) -0.18380(9) 0.0226(4) Uani 1 1 d . . . . .
H35 H 0.734327 0.463381 -0.225310 0.027 Uiso 1 1 calc R U . . .
C9 C 0.7645(2) 0.63407(17) -0.16099(9) 0.0222(4) Uani 1 1 d . . . . .
C10 C 0.85463(19) 0.70866(16) -0.10055(9) 0.0200(4) Uani 1 1 d . . . . .
H10 H 0.832882 0.791828 -0.085782 0.024 Uiso 1 1 calc R U . . .
C11 C 0.54621(19) 0.73480(16) 1.03548(9) 0.0188(3) Uani 1 1 d . . . . .
C12 C 0.4358(2) 0.60454(19) 1.08303(10) 0.0296(4) Uani 1 1 d . . . . .
H12A H 0.419273 0.516689 1.059939 0.035 Uiso 1 1 calc R U . . .
H12B H 0.351945 0.627784 1.111626 0.035 Uiso 1 1 calc R U . . .
C13 C 0.6016(2) 0.63014(16) 1.12884(9) 0.0217(4) Uani 1 1 d . . . . .
C14 C 0.6567(3) 0.58276(19) 1.17992(10) 0.0276(4) Uani 1 1 d . . . . .
C15 C 0.48106(19) 0.80954(16) 0.93105(8) 0.0188(4) Uani 1 1 d . . . . .
C16 C 0.5286(2) 0.89748(17) 0.90196(9) 0.0226(4) Uani 1 1 d . . . . .
C17 C 0.4548(2) 0.89884(19) 0.83602(10) 0.0273(4) Uani 1 1 d . . . . .
C18 C 0.3298(2) 0.81483(18) 0.79903(10) 0.0272(4) Uani 1 1 d . . . . .
C19 C 0.2796(2) 0.73057(18) 0.82891(9) 0.0258(4) Uani 1 1 d . . . . .
C20 C 0.3544(2) 0.72620(17) 0.89448(9) 0.0218(4) Uani 1 1 d . . . . .
C21 C 0.50664(19) 0.16562(16) 0.45350(8) 0.0179(3) Uani 1 1 d . . . . .
C22 C 0.3392(2) -0.00248(17) 0.40223(10) 0.0242(4) Uani 1 1 d . . . . .
C23 C 0.4509(2) -0.01525(16) 0.35044(9) 0.0213(4) Uani 1 1 d . . . . .
C24 C 0.4498(2) -0.10613(19) 0.29482(10) 0.0271(4) Uani 1 1 d . . . . .
C25 C 0.53592(19) 0.34324(16) 0.55679(8) 0.0176(3) Uani 1 1 d . . . . .
C26 C 0.5916(2) 0.46462(16) 0.57829(9) 0.0205(4) Uani 1 1 d . . . . .
C27 C 0.5545(2) 0.54059(17) 0.63739(9) 0.0218(4) Uani 1 1 d . . . . .
C28 C 0.4601(2) 0.49799(17) 0.67593(9) 0.0212(4) Uani 1 1 d . . . . .
C29 C 0.4062(2) 0.37694(17) 0.65453(9) 0.0223(4) Uani 1 1 d . . . . .
C30 C 0.4439(2) 0.29951(17) 0.59583(9) 0.0196(4) Uani 1 1 d . . . . .
C31 C 1.01888(19) 0.26699(15) 0.46493(8) 0.0172(3) Uani 1 1 d . . . . .
C32 C 0.8652(2) 0.39750(18) 0.41760(10) 0.0264(4) Uani 1 1 d . . . . .
H32A H 0.870324 0.485375 0.440718 0.032 Uiso 1 1 calc R U . . .
H32B H 0.755234 0.374597 0.389365 0.032 Uiso 1 1 calc R U . . .
C33 C 0.9894(2) 0.37113(16) 0.37108(9) 0.0202(4) Uani 1 1 d . . . . .
C34 C 0.9979(2) 0.41759(18) 0.31923(9) 0.0241(4) Uani 1 1 d . . . . .
C35 C 1.04295(19) 0.18992(15) 0.56855(8) 0.0176(3) Uani 1 1 d . . . . .
C36 C 1.1098(2) 0.09779(17) 0.59567(9) 0.0213(4) Uani 1 1 d . . . . .
C37 C 1.0900(2) 0.09244(18) 0.66032(9) 0.0238(4) Uani 1 1 d . . . . .
C38 C 1.0021(2) 0.17775(17) 0.69876(9) 0.0241(4) Uani 1 1 d . . . . .
C39 C 0.9334(2) 0.26746(17) 0.67106(9) 0.0240(4) Uani 1 1 d . . . . .
C40 C 0.9527(2) 0.27458(16) 0.60635(9) 0.0206(4) Uani 1 1 d . . . . .
H24 H 0.372(2) -0.1720(19) 0.2843(10) 0.030(5) Uiso 1 1 d . . . . .
H8 H 1.169(2) 0.1626(18) 0.4941(10) 0.028(5) Uiso 1 1 d . . . . .
H23 H 0.526(2) -0.1099(17) 0.2651(10) 0.026(5) Uiso 1 1 d . . . . .
H20 H 0.320(2) 0.6660(18) 0.9106(10) 0.024(5) Uiso 1 1 d . . . . .
H30 H 0.409(2) 0.2167(18) 0.5817(10) 0.025(5) Uiso 1 1 d . . . . .
H3 H 1.038(3) 1.149(2) 0.2253(11) 0.042(6) Uiso 1 1 d . . . . .
H22 H 0.345(2) -0.0745(17) 0.4199(9) 0.020(5) Uiso 1 1 d . . . . .
H27 H 0.592(2) 0.6210(18) 0.6500(9) 0.022(5) Uiso 1 1 d . . . . .
H33 H 0.919(2) 0.4739(18) 0.3091(10) 0.030(5) Uiso 1 1 d . . . . .
H14 H 0.588(2) 0.5268(18) 1.1898(10) 0.026(5) Uiso 1 1 d . . . . .
H25 H 0.672(3) 0.2912(19) 0.4876(10) 0.033(6) Uiso 1 1 d . . . . .
H26 H 0.655(2) 0.4931(17) 0.5514(10) 0.025(5) Uiso 1 1 d . . . . .
H9 H 0.681(2) 0.6678(17) -0.1867(10) 0.024(5) Uiso 1 1 d . . . . .
H39 H 0.871(2) 0.3298(18) 0.6975(10) 0.029(5) Uiso 1 1 d . . . . .
H40 H 0.908(2) 0.3380(17) 0.5901(9) 0.022(5) Uiso 1 1 d . . . . .
H38 H 0.988(2) 0.1756(18) 0.7439(11) 0.033(5) Uiso 1 1 d . . . . .
H29 H 0.342(2) 0.3467(18) 0.6808(10) 0.029(5) Uiso 1 1 d . . . . .
H37 H 1.133(2) 0.0270(19) 0.6765(11) 0.035(6) Uiso 1 1 d . . . . .
H7 H 0.946(2) 0.3827(18) -0.1595(9) 0.023(5) Uiso 1 1 d . . . . .
H16 H 0.614(2) 0.9550(17) 0.9270(9) 0.019(5) Uiso 1 1 d . . . . .
H19 H 0.188(2) 0.6741(19) 0.8050(10) 0.032(5) Uiso 1 1 d . . . . .
H5 H 0.668(3) 0.8406(18) 1.0063(10) 0.028(5) Uiso 1 1 d . . . . .
H2 H 0.921(2) 1.0766(18) 0.0811(10) 0.026(5) Uiso 1 1 d . . . . .
H36 H 1.169(2) 0.0385(18) 0.5690(10) 0.025(5) Uiso 1 1 d . . . . .
H0 H 1.175(3) 0.7058(19) 0.0103(11) 0.036(6) Uiso 1 1 d . . . . .
H28 H 0.432(2) 0.5496(18) 0.7174(10) 0.027(5) Uiso 1 1 d . . . . .
H17 H 0.488(2) 0.9626(19) 0.8168(10) 0.031(5) Uiso 1 1 d . . . . .
H34 H 1.081(2) 0.3952(17) 0.2899(10) 0.024(5) Uiso 1 1 d . . . . .
H13 H 0.764(2) 0.6029(18) 1.2069(10) 0.028(5) Uiso 1 1 d . . . . .
H18 H 0.279(2) 0.8157(17) 0.7533(10) 0.028(5) Uiso 1 1 d . . . . .
H4 H 1.205(3) 1.0766(19) 0.2450(11) 0.041(6) Uiso 1 1 d . . . . .
H21 H 0.229(3) 0.0043(19) 0.3797(11) 0.038(6) Uiso 1 1 d . . . . .
H1 H 0.825(2) 1.0010(17) 0.1162(9) 0.023(5) Uiso 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
S1 C3 1.7574(18) . ?
S1 C1 1.7846(16) . ?
S2 C13 1.7526(18) . ?
S2 C11 1.7866(17) . ?
S3 C23 1.7587(18) . ?
S3 C21 1.7844(17) . ?
S4 C33 1.7570(17) . ?
S4 C31 1.7846(16) . ?
N1 C1 1.278(2) . ?
N1 C2 1.462(2) . ?
N2 C1 1.357(2) . ?
N2 C5 1.411(2) . ?
N3 C11 1.278(2) . ?
N3 C12 1.458(2) . ?
N4 C11 1.357(2) . ?
N4 C15 1.408(2) . ?
N5 C21 1.280(2) . ?
N5 C22 1.460(2) . ?
N8 C31 1.355(2) . ?
N8 C35 1.412(2) . ?
N6 C21 1.356(2) . ?
N6 C25 1.408(2) . ?
N7 C31 1.279(2) . ?
N7 C32 1.457(2) . ?
C2 C3 1.521(2) . ?
C3 C4 1.319(3) . ?
C5 C10 1.392(2) . ?
C5 C6 1.393(2) . ?
C6 C7 1.383(2) . ?
C7 C8 1.387(2) . ?
C8 C9 1.381(3) . ?
C9 C10 1.388(2) . ?
C12 C13 1.510(2) . ?
C13 C14 1.317(2) . ?
C15 C20 1.390(3) . ?
C15 C16 1.394(2) . ?
C16 C17 1.383(2) . ?
C17 C18 1.386(3) . ?
C18 C19 1.379(3) . ?
C19 C20 1.389(2) . ?
C22 C23 1.521(2) . ?
C23 C24 1.321(3) . ?
C25 C30 1.391(2) . ?
C25 C26 1.396(2) . ?
C26 C27 1.377(3) . ?
C27 C28 1.389(2) . ?
C28 C29 1.389(3) . ?
C29 C30 1.380(2) . ?
C32 C33 1.518(2) . ?
C33 C34 1.323(2) . ?
C35 C40 1.390(2) . ?
C35 C36 1.395(2) . ?
C36 C37 1.383(2) . ?
C37 C38 1.388(3) . ?
C38 C39 1.382(3) . ?
C39 C40 1.389(2) . ?

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
C3 S1 C1 89.84(8) . . ?
C13 S2 C11 89.67(8) . . ?
C23 S3 C21 89.97(8) . . ?
C33 S4 C31 89.79(8) . . ?
C1 N1 C2 112.23(14) . . ?
C1 N2 C5 128.25(14) . . ?
C11 N3 C12 112.10(14) . . ?
C11 N4 C15 127.95(15) . . ?
C21 N5 C22 112.08(14) . . ?
C31 N8 C35 127.96(15) . . ?
C21 N6 C25 128.34(15) . . ?
C31 N7 C32 112.37(14) . . ?
N1 C1 N2 128.19(15) . . ?
N1 C1 S1 117.81(13) . . ?
N2 C1 S1 113.95(12) . . ?
N1 C2 C3 110.89(14) . . ?
C4 C3 C2 126.71(18) . . ?
C4 C3 S1 124.18(15) . . ?
C2 C3 S1 109.12(12) . . ?
C10 C5 C6 119.80(16) . . ?
C10 C5 N2 123.17(16) . . ?
C6 C5 N2 117.01(15) . . ?
C7 C6 C5 120.13(16) . . ?
C6 C7 C8 120.27(17) . . ?
C9 C8 C7 119.47(17) . . ?
C8 C9 C10 121.01(16) . . ?
C9 C10 C5 119.30(17) . . ?
N3 C11 N4 127.96(15) . . ?
N3 C11 S2 117.67(13) . . ?
N4 C11 S2 114.37(12) . . ?
N3 C12 C13 111.21(15) . . ?
C14 C13 C12 126.22(17) . . ?
C14 C13 S2 124.41(15) . . ?
C12 C13 S2 109.35(12) . . ?
C20 C15 C16 119.55(16) . . ?
C20 C15 N4 123.60(16) . . ?
C16 C15 N4 116.76(15) . . ?
C17 C16 C15 120.31(18) . . ?
C16 C17 C18 120.26(18) . . ?
C19 C18 C17 119.20(17) . . ?
C18 C19 C20 121.35(18) . . ?
C19 C20 C15 119.27(17) . . ?
N5 C21 N6 128.37(16) . . ?
N5 C21 S3 117.69(13) . . ?
N6 C21 S3 113.89(12) . . ?
N5 C22 C23 111.28(15) . . ?
C24 C23 C22 126.95(18) . . ?
C24 C23 S3 124.38(15) . . ?
C22 C23 S3 108.67(13) . . ?
C30 C25 C26 119.44(16) . . ?
C30 C25 N6 123.47(16) . . ?
C26 C25 N6 117.08(15) . . ?
C27 C26 C25 120.24(16) . . ?
C26 C27 C28 120.59(18) . . ?
C29 C28 C27 118.87(17) . . ?
C30 C29 C28 121.13(17) . . ?
C29 C30 C25 119.71(17) . . ?
N7 C31 N8 127.79(15) . . ?
N7 C31 S4 117.65(12) . . ?
N8 C31 S4 114.56(12) . . ?
N7 C32 C33 111.05(14) . . ?
C34 C33 C32 126.41(16) . . ?
C34 C33 S4 124.43(15) . . ?
C32 C33 S4 109.14(12) . . ?
C40 C35 C36 119.42(16) . . ?
C40 C35 N8 123.89(15) . . ?
C36 C35 N8 116.59(15) . . ?
C37 C36 C35 120.32(17) . . ?
C36 C37 C38 120.53(17) . . ?
C39 C38 C37 118.91(17) . . ?
C38 C39 C40 121.32(18) . . ?
C39 C40 C35 119.48(16) . . ?

_refine_diff_density_max         0.329
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.052



####################################################################### 
# 
# 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_c539
_database_code_depnum_ccdc_archive 'CCDC 2234523'
loop_
_audit_author_name
_audit_author_address
'M. Concepcion Gimeno'
;Instituto de Sintesis Quimica y Catalisis Homogenea
Spain
;
_audit_update_record             
;
2023-01-05 deposited with the CCDC.	2023-02-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H12 N2 S'
_chemical_formula_weight         204.29

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'

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

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

_cell_length_a                   24.2242(5)
_cell_length_b                   14.3455(3)
_cell_length_c                   11.8463(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4116.66(15)
_cell_formula_units_Z            16
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9500
_cell_measurement_theta_min      3.7180
_cell_measurement_theta_max      30.9660

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_F_000             1728
_exptl_transmission_factor_min   0.855
_exptl_transmission_factor_max   1.266
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.274
_shelx_estimated_absorpt_T_min   0.903
_shelx_estimated_absorpt_T_max   0.957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.89609
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41r (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω rotations'
_diffrn_detector_area_resol_mean 16.0655
_diffrn_reflns_number            29468
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.301
_diffrn_reflns_theta_max         31.134
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.920
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.920
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.920
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6109
_reflns_number_gt                5108
_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       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_structure_solution    SHELXS
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0452P)²+1.8075P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   diffmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6109
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0364
_refine_ls_wR_factor_ref         0.0945
_refine_ls_wR_factor_gt          0.0880
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.68123(5) 1.13972(9) 0.81230(11) 0.0203(2) Uani 1 1 d . . . . .
C2 C 0.68350(6) 1.21408(9) 0.74614(12) 0.0260(3) Uani 1 1 d . . . . .
H2A H 0.694290 1.272632 0.776422 0.031 Uiso 1 1 calc R U . . .
H2B H 0.674345 1.208845 0.668425 0.031 Uiso 1 1 calc R U . . .
C3 C 0.69450(6) 1.13723(9) 0.93668(11) 0.0235(3) Uani 1 1 d . . . . .
H3A H 0.729475 1.170716 0.951730 0.028 Uiso 1 1 calc R U . . .
H3B H 0.664665 1.167425 0.980546 0.028 Uiso 1 1 calc R U . . .
C4 C 0.71364(6) 1.01573(10) 1.08371(11) 0.0292(3) Uani 1 1 d . . . . .
H4A H 0.680505 1.019342 1.130975 0.044 Uiso 1 1 calc R U . . .
H4B H 0.741527 1.059209 1.112318 0.044 Uiso 1 1 calc R U . . .
H4C H 0.728358 0.952120 1.085725 0.044 Uiso 1 1 calc R U . . .
C5 C 0.67745(5) 0.97600(8) 0.89725(10) 0.0168(2) Uani 1 1 d . . . . .
C6 C 0.65045(5) 0.82944(8) 0.83715(10) 0.0177(2) Uani 1 1 d . . . . .
C7 C 0.59788(5) 0.79010(9) 0.84458(10) 0.0201(2) Uani 1 1 d . . . . .
H7 H 0.574356 0.806193 0.905717 0.024 Uiso 1 1 calc R U . . .
C8 C 0.57970(5) 0.72741(9) 0.76293(11) 0.0221(2) Uani 1 1 d . . . . .
H8 H 0.543735 0.701371 0.768205 0.027 Uiso 1 1 calc R U . . .
C9 C 0.61402(6) 0.70279(9) 0.67366(11) 0.0222(2) Uani 1 1 d . . . . .
H9 H 0.601666 0.659684 0.618265 0.027 Uiso 1 1 calc R U . . .
C10 C 0.66641(5) 0.74150(9) 0.66586(11) 0.0210(2) Uani 1 1 d . . . . .
H10 H 0.689856 0.725016 0.604756 0.025 Uiso 1 1 calc R U . . .
C11 C 0.68470(5) 0.80422(8) 0.74699(10) 0.0195(2) Uani 1 1 d . . . . .
H11 H 0.720672 0.830157 0.741265 0.023 Uiso 1 1 calc R U . . .
C12 C 0.63419(5) 0.51581(9) -0.04764(11) 0.0202(2) Uani 1 1 d . . . . .
C13 C 0.67385(6) 0.55485(11) -0.10866(13) 0.0293(3) Uani 1 1 d . . . . .
H13A H 0.678084 0.620688 -0.108970 0.035 Uiso 1 1 calc R U . . .
H13B H 0.698030 0.516978 -0.152061 0.035 Uiso 1 1 calc R U . . .
C14 C 0.59312(5) 0.56732(9) 0.02481(11) 0.0222(2) Uani 1 1 d . . . . .
H14A H 0.612599 0.604584 0.082776 0.027 Uiso 1 1 calc R U . . .
H14B H 0.570729 0.610056 -0.022199 0.027 Uiso 1 1 calc R U . . .
C15 C 0.51923(5) 0.52855(9) 0.16418(10) 0.0209(2) Uani 1 1 d . . . . .
H15A H 0.492385 0.478773 0.178200 0.031 Uiso 1 1 calc R U . . .
H15B H 0.499864 0.584625 0.138388 0.031 Uiso 1 1 calc R U . . .
H15C H 0.539249 0.542445 0.234067 0.031 Uiso 1 1 calc R U . . .
C16 C 0.56816(5) 0.40714(8) 0.05947(9) 0.0161(2) Uani 1 1 d . . . . .
C17 C 0.55058(5) 0.24775(8) 0.07578(10) 0.0175(2) Uani 1 1 d . . . . .
C18 C 0.56614(5) 0.18134(9) 0.15608(11) 0.0209(2) Uani 1 1 d . . . . .
H18 H 0.573090 0.199977 0.231707 0.025 Uiso 1 1 calc R U . . .
C19 C 0.57149(5) 0.08807(9) 0.12577(12) 0.0246(3) Uani 1 1 d . . . . .
H19 H 0.582353 0.043559 0.180828 0.030 Uiso 1 1 calc R U . . .
C20 C 0.56112(5) 0.05943(9) 0.01597(12) 0.0254(3) Uani 1 1 d . . . . .
H20 H 0.565103 -0.004258 -0.004441 0.031 Uiso 1 1 calc R U . . .
C21 C 0.54485(5) 0.12481(9) -0.06383(12) 0.0252(3) Uani 1 1 d . . . . .
H21 H 0.537540 0.105647 -0.139123 0.030 Uiso 1 1 calc R U . . .
C22 C 0.53920(5) 0.21812(9) -0.03429(11) 0.0207(2) Uani 1 1 d . . . . .
H22 H 0.527515 0.262092 -0.089287 0.025 Uiso 1 1 calc R U . . .
N1 N 0.69961(5) 1.04016(8) 0.96846(9) 0.0215(2) Uani 1 1 d . . . . .
N2 N 0.66936(4) 0.89067(7) 0.92272(9) 0.0199(2) Uani 1 1 d . . . . .
N3 N 0.55798(4) 0.49868(7) 0.07816(9) 0.0180(2) Uani 1 1 d . . . . .
N4 N 0.54262(4) 0.34122(7) 0.10957(9) 0.0189(2) Uani 1 1 d . . . . .
S1 S 0.66095(2) 1.02857(2) 0.76518(3) 0.01908(8) Uani 1 1 d . . . . .
S2 S 0.62257(2) 0.39423(2) -0.04176(3) 0.01992(8) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.3247(18) . ?
C1 C3 1.5086(18) . ?
C1 S1 1.7594(13) . ?
C3 N1 1.4478(17) . ?
C4 N1 1.4499(17) . ?
C5 N2 1.2759(16) . ?
C5 N1 1.3590(15) . ?
C5 S1 1.7822(12) . ?
C6 C7 1.3957(17) . ?
C6 C11 1.4000(17) . ?
C6 N2 1.4174(15) . ?
C7 C8 1.3921(18) . ?
C8 C9 1.3907(19) . ?
C9 C10 1.3884(18) . ?
C10 C11 1.3891(18) . ?
C12 C13 1.3264(18) . ?
C12 C14 1.5075(18) . ?
C12 S2 1.7682(13) . ?
C14 N3 1.4468(16) . ?
C15 N3 1.4502(15) . ?
C16 N4 1.2763(15) . ?
C16 N3 1.3544(15) . ?
C16 S2 1.7916(12) . ?
C17 C18 1.3981(17) . ?
C17 C22 1.3990(17) . ?
C17 N4 1.4126(15) . ?
C18 C19 1.3913(18) . ?
C19 C20 1.387(2) . ?
C20 C21 1.389(2) . ?
C21 C22 1.3902(18) . ?

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 C3 126.02(12) . . ?
C2 C1 S1 123.62(11) . . ?
C3 C1 S1 110.36(9) . . ?
N1 C3 C1 107.15(10) . . ?
N2 C5 N1 124.31(11) . . ?
N2 C5 S1 125.39(9) . . ?
N1 C5 S1 110.29(9) . . ?
C7 C6 C11 118.97(11) . . ?
C7 C6 N2 120.03(11) . . ?
C11 C6 N2 120.94(11) . . ?
C8 C7 C6 120.39(12) . . ?
C9 C8 C7 120.22(12) . . ?
C10 C9 C8 119.70(12) . . ?
C9 C10 C11 120.30(11) . . ?
C10 C11 C6 120.41(12) . . ?
C13 C12 C14 125.55(13) . . ?
C13 C12 S2 123.60(11) . . ?
C14 C12 S2 110.85(9) . . ?
N3 C14 C12 107.66(10) . . ?
N4 C16 N3 123.66(11) . . ?
N4 C16 S2 126.24(9) . . ?
N3 C16 S2 110.09(8) . . ?
C18 C17 C22 118.70(11) . . ?
C18 C17 N4 119.40(11) . . ?
C22 C17 N4 121.72(11) . . ?
C19 C18 C17 120.32(12) . . ?
C20 C19 C18 120.67(12) . . ?
C19 C20 C21 119.32(12) . . ?
C20 C21 C22 120.46(13) . . ?
C21 C22 C17 120.52(12) . . ?
C5 N1 C3 117.15(10) . . ?
C5 N1 C4 120.88(11) . . ?
C3 N1 C4 119.83(11) . . ?
C5 N2 C6 118.37(10) . . ?
C16 N3 C14 118.78(10) . . ?
C16 N3 C15 121.27(10) . . ?
C14 N3 C15 119.12(10) . . ?
C16 N4 C17 120.36(10) . . ?
C1 S1 C5 92.43(6) . . ?
C12 S2 C16 92.38(6) . . ?

_refine_diff_density_max         0.388
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.055



####################################################################### 
# 
# 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_c567
_database_code_depnum_ccdc_archive 'CCDC 2234527'
loop_
_audit_author_name
_audit_author_address
'M. Concepcion Gimeno'
;Instituto de Sintesis Quimica y Catalisis Homogenea
Spain
;
_audit_update_record             
;
2023-02-17 deposited with the CCDC.	2023-02-22 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT910_c567                
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         12 Note
RESPONSE: Some reflections are missing due to geometry of the experiment.
;
# Added during the CSD deposition process: Friday 17 February 2023 06:37 PM
# end Validation Reply Form

_audit_creation_date             2023-01-31
_audit_creation_method           
;
Olex2 1.5-dev
(compiled 2023.01.20 svn.r024a95a1 for OlexSys, GUI svn.r6444)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C35 H29 Au F2 N3 P S2, C F3 O3 S'
_chemical_formula_sum            'C36 H29 Au F5 N3 O3 P S3'
_chemical_formula_weight         970.74
_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 0.0033 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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'

_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      trigonal
_space_group_IT_number           154
_space_group_name_H-M_alt        'P 32 2 1'
_space_group_name_Hall           'P 32 2"'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
'x-y, -y, -z+1/3'
'-x, -x+y, -z+2/3'
'y, x, -z'

_cell_length_a                   13.8662(2)
_cell_length_b                   13.8662(2)
_cell_length_c                   32.5715(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     5423.57(19)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    14146
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.3010
_cell_measurement_theta_min      3.4890
_shelx_estimated_absorpt_T_max   0.695
_shelx_estimated_absorpt_T_min   0.492
_exptl_absorpt_coefficient_mu    4.353
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60239
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.783
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             2862
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            27642
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_min         3.193
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 16.0655
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω rotations'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.773
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                6297
_reflns_number_total             6726
_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       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-dev (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-dev (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    SHELXS
_refine_diff_density_max         0.931
_refine_diff_density_min         -0.889
_refine_diff_density_rms         0.094
_refine_ls_abs_structure_details 
;
 Flack x determined using 2529 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.012(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     617
_refine_ls_number_reflns         6726
_refine_ls_number_restraints     1501
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0370
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0429P)²+12.5958P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0888
_refine_ls_wR_factor_ref         0.0914
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C1A-F3 = C1A-F4 = C1A-F5
 1.33 with sigma of 0.02
 C1A-S6
 1.82 with sigma of 0.02
 S6-O7 = S6-O8 = S6-O9
 1.44 with sigma of 0.02
 C1A-O7
 2.58 with sigma of 0.04
 C1A-O8
 2.56 with sigma of 0.04
 C1A-O9
 2.57 with sigma of 0.04
 N3-C5 \\sim N3A-C5
 with sigma of 0.02
 N3-C6 \\sim N3A-C6A
 with sigma of 0.02
 F1-C10 \\sim F1A-C10A
 with sigma of 0.02
 C6-C7 \\sim C6A-C7A
 with sigma of 0.02
 C6-C11 \\sim C6A-C11A
 with sigma of 0.02
 C7-C8 \\sim C7A-C8A
 with sigma of 0.02
 C8-C9 \\sim C8A-C9A
 with sigma of 0.02
 C9-C10 \\sim C9A-C10A
 with sigma of 0.02
 C10-C11 \\sim C10A-C11A
 with sigma of 0.02
 N3-C7 \\sim N3A-C7A
 with sigma of 0.04
 N3-C11 \\sim N3A-C11A
 with sigma of 0.04
 F1-C9 \\sim F1A-C9A
 with sigma of 0.04
 F1-C11 \\sim F1A-C11A
 with sigma of 0.04
 C5-C6 \\sim C5-C6A
 with sigma of 0.04
 C6-C8 \\sim C6A-C8A
 with sigma of 0.04
 C6-C10 \\sim C6A-C10A
 with sigma of 0.04
 C7-C9 \\sim C7A-C9A
 with sigma of 0.04
 C7-C11 \\sim C7A-C11A
 with sigma of 0.04
 C8-C10 \\sim C8A-C10A
 with sigma of 0.04
 C9-C11 \\sim C9A-C11A
 with sigma of 0.04
 N2-C1 \\sim N2A-C1
 with sigma of 0.02
 N2-C12 \\sim N2A-C12A
 with sigma of 0.02
 F2-C16 \\sim F2A-C16A
 with sigma of 0.02
 C12-C13 \\sim C12A-C13A
 with sigma of 0.02
 C12-C17 \\sim C12A-C17A
 with sigma of 0.02
 C13-C14 \\sim C13A-C14A
 with sigma of 0.02
 C14-C15 \\sim C14A-C15A
 with sigma of 0.02
 C15-C16 \\sim C15A-C16A
 with sigma of 0.02
 C16-C17 \\sim C16A-C17A
 with sigma of 0.02
 N2-C13 \\sim N2A-C13A
 with sigma of 0.04
 N2-C17 \\sim N2A-C17A
 with sigma of 0.04
 F2-C15 \\sim F2A-C15A
 with sigma of 0.04
 F2-C17 \\sim F2A-C17A
 with sigma of 0.04
 C1-C12 \\sim C1-C12A
 with sigma of 0.04
 C12-C14 \\sim C12A-C14A
 with sigma of 0.04
 C12-C16 \\sim C12A-C16A
 with sigma of 0.04
 C13-C15 \\sim C13A-C15A
 with sigma of 0.04
 C13-C17 \\sim C13A-C17A
 with sigma of 0.04
 C14-C16 \\sim C14A-C16A
 with sigma of 0.04
 C15-C17 \\sim C15A-C17A
 with sigma of 0.04
 C17-F2 \\sim F2-C15
 with sigma of 0.001
 C17A-F2A \\sim F2A-C15A
 with sigma of 0.001
 C1A-F3 \\sim C1A-F4 \\sim C1A-F5
 with sigma of 0.02
 F3-F4 \\sim F4-F5 \\sim F5-F3
 with sigma of 0.04
 S6-F3 \\sim S6-F4 \\sim S6-F5
 with sigma of 0.04
 S6-O7 \\sim S6-O8 \\sim S6-O9
 with sigma of 0.02
 O7-O8 \\sim O8-O9 \\sim O7-O9
 with sigma of 0.04
 C1A-O7 \\sim C1A-O8 \\sim C1A-O9
 with sigma of 0.04
 C1A-F3 \\sim C1B-F3A
 with sigma of 0.02
 C1A-F4 \\sim C1B-F4A
 with sigma of 0.02
 C1A-F5 \\sim C1B-F5A
 with sigma of 0.02
 C1A-S6 \\sim C1B-S6A
 with sigma of 0.02
 S6-O7 \\sim S6A-O7A
 with sigma of 0.02
 S6-O8 \\sim S6A-O8A
 with sigma of 0.02
 S6-O9 \\sim S6A-O9A
 with sigma of 0.02
 C1A-O7 \\sim C1B-O7A
 with sigma of 0.04
 C1A-O8 \\sim C1B-O8A
 with sigma of 0.04
 C1A-O9 \\sim C1B-O9A
 with sigma of 0.04
 F3-F4 \\sim F3A-F4A
 with sigma of 0.04
 F3-F5 \\sim F3A-F5A
 with sigma of 0.04
 F3-S6 \\sim F3A-S6A
 with sigma of 0.04
 F4-F5 \\sim F4A-F5A
 with sigma of 0.04
 F4-S6 \\sim F4A-S6A
 with sigma of 0.04
 F5-S6 \\sim F5A-S6A
 with sigma of 0.04
 O7-O8 \\sim O7A-O8A
 with sigma of 0.04
 O7-O9 \\sim O7A-O9A
 with sigma of 0.04
 O8-O9 \\sim O8A-O9A
 with sigma of 0.04
3. Restrained planarity
 F2, C16, C15, C14, C13, C12, C17
 with sigma of 0.001
 N2, F2, C16, C15, C14, C13, C12, C17
 with sigma of 0.001
4. Rigid bond restraints
 C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C16, C15, C14, C13, C12, C17,
 C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30, C31, C32, C33,
  C34, C35, C6A, C7A, C8A, C9A, C10A, C11A, C12A, C13A, C14A, C15A, C16A, C17A,
 C1A, C1B, N1, N2, N3, N3A, N2A, F1, F2, F1A, F2A, F3, F4, F5, F4A, F3A, F5A,
 O7, O8, O9, O7A, O8A, O9A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
Uanis(N2) \\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C15)
\\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C12) \\sim Ueq,
Uanis(C17) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
6. Rigid body (RIGU) restrains
 F2A, C12A, C13A, C14A, C15A, C16A, C17A, N2A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F1A, C6A, C7A, C8A, C9A, C10A, C11A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N2, F2, C16, C15, C14, C13, C12, C17
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C1A, F3, F4, F5, S6, O7, O8, O9
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 S6, C1A, F3, F4, F5, O7, O8, O9
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F5A, F4A, C1B, F3A, S6A, O7A, O8A, O9A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
7. Others
 Sof(F1A)=Sof(C6A)=Sof(C7A)=Sof(H7A)=Sof(C8A)=Sof(H8A)=Sof(C9A)=Sof(H9A)=
 Sof(C10A)=Sof(C11A)=Sof(H11A)=Sof(N3A)=1-FVAR(1)
 Sof(N3)=Sof(F1)=Sof(C6)=Sof(C7)=Sof(H7)=Sof(C8)=Sof(H8)=Sof(C9)=Sof(H9)=
 Sof(C10)=Sof(C11)=Sof(H11)=FVAR(1)
 Sof(F2A)=Sof(C12A)=Sof(C13A)=Sof(H13A)=Sof(C14A)=Sof(H14A)=Sof(C15A)=
 Sof(H15A)=Sof(C16A)=Sof(C17A)=Sof(H17A)=Sof(N2A)=Sof(H2AA)=1-FVAR(2)
 Sof(N2)=Sof(H2)=Sof(F2)=Sof(C16)=Sof(C15)=Sof(H15)=Sof(C14)=Sof(H14)=Sof(C13)=
 Sof(H13)=Sof(C12)=Sof(C17)=Sof(H17)=FVAR(2)
 Sof(F4A)=Sof(C1B)=Sof(F3A)=Sof(F5A)=Sof(S6A)=Sof(O7A)=Sof(O8A)=Sof(O9A)=1-
 FVAR(3)
 Sof(C1A)=Sof(F3)=Sof(F4)=Sof(F5)=Sof(S6)=Sof(O7)=Sof(O8)=Sof(O9)=FVAR(3)
8.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
8.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C7(H7), C8(H8), C9(H9), C11(H11), C15(H15), C14(H14), C13(H13),
 C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C25(H25), C26(H26),
  C27(H27), C28(H28), C29(H29), C31(H31), C32(H32), C33(H33), C34(H34),
 C35(H35), C7A(H7A), C8A(H8A), C9A(H9A), C11A(H11A), C13A(H13A), C14A(H14A),
 C15A(H15A), C17A(H17A), N2A(H2AA)
8.c Fitted hexagon refined as free rotating group:
 C6(C7,C8,C9,C10,C11), C16(C15,C14,C13,C12,C17), C18(C19,C20,C21,C22,C23),
 C24(C25,C26,C27,C28,C29), C30(C31,C32,C33,C34,C35), C12A(C13A,C14A,C15A,C16A,
 C17A)
8.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_atom_sites_solution_hydrogens   geom
_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 0.34346(3) 0.12686(3) 0.67421(2) 0.04461(12) Uani 1 1 d . . . . .
S1 S 0.4314(2) 0.0640(2) 0.71917(7) 0.0496(6) Uani 1 1 d . U . . .
S2 S 0.3938(2) -0.0142(2) 0.87592(7) 0.0509(6) Uani 1 1 d . U . . .
P1 P 0.2681(2) 0.1896(2) 0.62650(8) 0.0489(6) Uani 1 1 d . U . . .
N1 N 0.4156(7) 0.0568(7) 0.7999(2) 0.0445(17) Uani 1 1 d . U . . .
N2 N 0.439(3) 0.2192(12) 0.7710(4) 0.050(7) Uani 0.320(17) 1 d D U P A 1
H2 H 0.427092 0.232093 0.796379 0.060 Uiso 0.320(17) 1 calc R U P A 1
N3 N 0.4275(16) 0.1869(13) 0.8481(5) 0.040(5) Uani 0.646(18) 1 d D U P B 1
F1 F 0.3088(14) 0.3305(13) 0.9568(4) 0.111(6) Uani 0.646(18) 1 d D U P B 1
F2 F 0.7046(13) 0.4844(5) 0.67653(15) 0.097(8) Uani 0.320(17) 1 d D U P A 1
C1 C 0.4350(8) 0.1223(9) 0.7663(3) 0.047(2) Uani 1 1 d D U . . .
C2 C 0.3979(10) -0.0568(9) 0.7959(3) 0.052(3) Uani 1 1 d . U . . .
H2A H 0.467483 -0.053754 0.786824 0.063 Uiso 1 1 calc R U . . .
H2B H 0.339272 -0.099127 0.775296 0.063 Uiso 1 1 calc R U . . .
C3 C 0.3635(10) -0.1123(9) 0.8367(3) 0.053(3) Uani 1 1 d . U . . .
C4 C 0.3195(10) -0.2201(10) 0.8433(3) 0.059(3) Uani 1 1 d . U . . .
H4A H 0.377586 -0.235477 0.852787 0.089 Uiso 1 1 calc R U . . .
H4B H 0.287181 -0.260783 0.817696 0.089 Uiso 1 1 calc R U . . .
H4C H 0.261239 -0.244186 0.864217 0.089 Uiso 1 1 calc R U . . .
C5 C 0.4214(9) 0.0921(9) 0.8407(3) 0.048(2) Uani 1 1 d D U . . .
C6 C 0.4383(14) 0.2247(13) 0.8892(4) 0.047(4) Uani 0.646(18) 1 d DG U P B 1
C7 C 0.5273(12) 0.2398(12) 0.9134(4) 0.054(4) Uani 0.646(18) 1 d DG U P B 1
H7 H 0.578833 0.219424 0.903214 0.064 Uiso 0.646(18) 1 calc R U P B 1
C8 C 0.5410(12) 0.2847(13) 0.9526(4) 0.055(4) Uani 0.646(18) 1 d DG U P B 1
H8 H 0.601879 0.295054 0.969125 0.066 Uiso 0.646(18) 1 calc R U P B 1
C9 C 0.4657(14) 0.3146(14) 0.9675(4) 0.065(5) Uani 0.646(18) 1 d DG U P B 1
H9 H 0.475028 0.345301 0.994269 0.078 Uiso 0.646(18) 1 calc R U P B 1
C10 C 0.3766(14) 0.2995(16) 0.9433(5) 0.069(5) Uani 0.646(18) 1 d DG U P B 1
C11 C 0.3629(13) 0.2546(16) 0.9041(5) 0.060(5) Uani 0.646(18) 1 d DG U P B 1
H11 H 0.302084 0.244288 0.887593 0.072 Uiso 0.646(18) 1 calc R U P B 1
C16 C 0.5970(12) 0.4382(4) 0.69617(13) 0.070(6) Uani 0.320(17) 1 d DG U P A 1
C15 C 0.5272(12) 0.4804(7) 0.6870(2) 0.070(7) Uani 0.320(17) 1 d DG U P A 1
H15 H 0.550212 0.539489 0.667815 0.085 Uiso 0.320(17) 1 calc R U P A 1
C14 C 0.4238(12) 0.4360(10) 0.7059(3) 0.065(6) Uani 0.320(17) 1 d DG U P A 1
H14 H 0.376057 0.464778 0.699609 0.077 Uiso 0.320(17) 1 calc R U P A 1
C13 C 0.3901(12) 0.3495(10) 0.7339(3) 0.061(6) Uani 0.320(17) 1 d DG U P A 1
H13 H 0.319385 0.319157 0.746849 0.073 Uiso 0.320(17) 1 calc R U P A 1
C12 C 0.4599(13) 0.3074(7) 0.7431(2) 0.060(6) Uani 0.320(17) 1 d DG U P A 1
C17 C 0.5633(13) 0.3517(5) 0.72423(17) 0.067(6) Uani 0.320(17) 1 d DG U P A 1
H17 H 0.611023 0.322955 0.730502 0.081 Uiso 0.320(17) 1 calc R U P A 1
C18 C 0.1569(6) 0.2116(6) 0.6460(2) 0.060(3) Uani 1 1 d G U . . .
C19 C 0.0709(6) 0.1999(7) 0.62076(19) 0.074(3) Uani 1 1 d G U . . .
H19 H 0.069566 0.180968 0.592658 0.089 Uiso 1 1 calc R U . . .
C20 C -0.0131(6) 0.2160(8) 0.6366(3) 0.082(4) Uani 1 1 d G U . . .
H20 H -0.071839 0.208039 0.619319 0.099 Uiso 1 1 calc R U . . .
C21 C -0.0111(7) 0.2438(8) 0.6777(3) 0.081(4) Uani 1 1 d G U . . .
H21 H -0.068540 0.254751 0.688542 0.097 Uiso 1 1 calc R U . . .
C22 C 0.0748(8) 0.2554(7) 0.7030(2) 0.083(3) Uani 1 1 d G U . . .
H22 H 0.076163 0.274391 0.731104 0.100 Uiso 1 1 calc R U . . .
C23 C 0.1588(6) 0.2393(7) 0.6872(2) 0.072(3) Uani 1 1 d G U . . .
H23 H 0.217569 0.247321 0.704443 0.086 Uiso 1 1 calc R U . . .
C24 C 0.3761(5) 0.3178(5) 0.6050(3) 0.059(3) Uani 1 1 d G U . . .
C25 C 0.4802(6) 0.3278(5) 0.5997(2) 0.049(2) Uani 1 1 d G U . . .
H25 H 0.493600 0.270958 0.609430 0.059 Uiso 1 1 calc R U . . .
C26 C 0.5646(5) 0.4210(7) 0.5802(3) 0.066(3) Uani 1 1 d G U . . .
H26 H 0.635775 0.427826 0.576566 0.080 Uiso 1 1 calc R U . . .
C27 C 0.5450(6) 0.5041(6) 0.5660(4) 0.119(6) Uani 1 1 d G U . . .
H27 H 0.602708 0.567817 0.552642 0.143 Uiso 1 1 calc R U . . .
C28 C 0.4409(8) 0.4941(7) 0.5713(4) 0.151(8) Uani 1 1 d G U . . .
H28 H 0.427466 0.550941 0.561582 0.181 Uiso 1 1 calc R U . . .
C29 C 0.3564(6) 0.4009(7) 0.5908(4) 0.110(6) Uani 1 1 d G U . . .
H29 H 0.285289 0.394072 0.594446 0.131 Uiso 1 1 calc R U . . .
C30 C 0.2080(6) 0.0987(5) 0.58241(17) 0.057(3) Uani 1 1 d G U . . .
C31 C 0.1153(7) -0.0058(6) 0.58877(19) 0.075(3) Uani 1 1 d G U . . .
H31 H 0.086176 -0.028327 0.615672 0.090 Uiso 1 1 calc R U . . .
C32 C 0.0652(7) -0.0772(5) 0.5558(3) 0.084(4) Uani 1 1 d G U . . .
H32 H 0.001858 -0.148658 0.560108 0.101 Uiso 1 1 calc R U . . .
C33 C 0.1078(7) -0.0442(6) 0.5164(2) 0.077(3) Uani 1 1 d G U . . .
H33 H 0.073590 -0.093076 0.493841 0.093 Uiso 1 1 calc R U . . .
C34 C 0.2005(7) 0.0603(7) 0.51004(16) 0.071(3) Uani 1 1 d G U . . .
H34 H 0.229640 0.082838 0.483137 0.085 Uiso 1 1 calc R U . . .
C35 C 0.2506(6) 0.1318(6) 0.5430(2) 0.061(3) Uani 1 1 d G U . . .
H35 H 0.313959 0.203171 0.538701 0.073 Uiso 1 1 calc R U . . .
F1A F 0.626(2) 0.248(2) 0.9836(7) 0.123(11) Uani 0.354(18) 1 d D U P B 2
C6A C 0.474(3) 0.229(3) 0.8932(8) 0.043(7) Uani 0.354(18) 1 d D U P B 2
C7A C 0.413(3) 0.278(3) 0.9062(9) 0.051(7) Uani 0.354(18) 1 d D U P B 2
H7A H 0.365198 0.287252 0.887759 0.061 Uiso 0.354(18) 1 calc R U P B 2
C8A C 0.424(3) 0.314(3) 0.9463(9) 0.060(7) Uani 0.354(18) 1 d D U P B 2
H8A H 0.384086 0.348753 0.955445 0.072 Uiso 0.354(18) 1 calc R U P B 2
C9A C 0.492(4) 0.298(4) 0.9734(12) 0.080(8) Uani 0.354(18) 1 d D U P B 2
H9A H 0.498251 0.321626 1.001181 0.095 Uiso 0.354(18) 1 calc R U P B 2
C10A C 0.552(3) 0.249(3) 0.9598(9) 0.066(7) Uani 0.354(18) 1 d D U P B 2
C11A C 0.539(3) 0.210(3) 0.9205(9) 0.060(8) Uani 0.354(18) 1 d D U P B 2
H11A H 0.574022 0.169826 0.911913 0.073 Uiso 0.354(18) 1 calc R U P B 2
N3A N 0.463(3) 0.195(2) 0.8513(8) 0.034(7) Uani 0.354(18) 1 d D U P B 2
F2A F 0.3693(18) 0.4818(13) 0.7045(6) 0.193(8) Uani 0.680(17) 1 d D U P A 2
C12A C 0.4949(12) 0.3125(8) 0.7416(3) 0.064(4) Uani 0.680(17) 1 d DG U P A 2
C13A C 0.5907(12) 0.3554(11) 0.7178(4) 0.117(6) Uani 0.680(17) 1 d DG U P A 2
H13A H 0.638970 0.325475 0.720126 0.141 Uiso 0.680(17) 1 calc R U P A 2
C14A C 0.6160(12) 0.4420(11) 0.6906(3) 0.141(7) Uani 0.680(17) 1 d DG U P A 2
H14A H 0.681503 0.471360 0.674291 0.170 Uiso 0.680(17) 1 calc R U P A 2
C15A C 0.5454(14) 0.4858(10) 0.6872(4) 0.158(8) Uani 0.680(17) 1 d DG U P A 2
H15A H 0.562691 0.545036 0.668579 0.189 Uiso 0.680(17) 1 calc R U P A 2
C16A C 0.4496(13) 0.4429(10) 0.7110(4) 0.121(6) Uani 0.680(17) 1 d DG U P A 2
C17A C 0.4243(12) 0.3563(9) 0.7382(3) 0.090(5) Uani 0.680(17) 1 d DG U P A 2
H17A H 0.358811 0.326943 0.754535 0.108 Uiso 0.680(17) 1 calc R U P A 2
N2A N 0.4623(17) 0.2273(10) 0.7723(4) 0.052(4) Uani 0.680(17) 1 d D U P A 2
H2AA H 0.460188 0.247101 0.797758 0.063 Uiso 0.680(17) 1 calc R U P A 2
C1A C 0.2021(16) 0.3709(16) 0.8780(6) 0.101(6) Uani 0.525(13) 1 d D U P C 1
F3 F 0.1174(18) 0.385(2) 0.8810(9) 0.160(9) Uani 0.525(13) 1 d D U P C 1
F4 F 0.2750(19) 0.434(2) 0.9060(7) 0.191(12) Uani 0.525(13) 1 d D U P C 1
F5 F 0.1649(19) 0.2637(16) 0.8826(9) 0.130(8) Uani 0.525(13) 1 d D U P C 1
S6 S 0.2751(11) 0.4179(13) 0.8302(5) 0.109(6) Uani 0.525(13) 1 d D U P C 1
O7 O 0.1926(16) 0.3543(19) 0.7990(6) 0.106(7) Uani 0.525(13) 1 d D U P C 1
O8 O 0.300(3) 0.5290(17) 0.8261(10) 0.183(14) Uani 0.525(13) 1 d D U P C 1
O9 O 0.3633(16) 0.395(2) 0.8330(7) 0.100(9) Uani 0.525(13) 1 d D U P C 1
F4A F 0.104(2) 0.404(3) 0.8446(8) 0.166(9) Uani 0.475(13) 1 d D U P C 2
C1B C 0.1449(17) 0.336(2) 0.8419(7) 0.106(6) Uani 0.475(13) 1 d D U P C 2
F3A F 0.0729(19) 0.252(2) 0.8206(9) 0.180(10) Uani 0.475(13) 1 d D U P C 2
F5A F 0.143(2) 0.305(3) 0.8791(8) 0.153(11) Uani 0.475(13) 1 d D U P C 2
S6A S 0.2806(13) 0.4129(13) 0.8196(5) 0.077(4) Uani 0.475(13) 1 d D U P C 2
O7A O 0.259(2) 0.437(3) 0.7792(6) 0.118(9) Uani 0.475(13) 1 d D U P C 2
O8A O 0.340(2) 0.501(3) 0.8463(10) 0.166(14) Uani 0.475(13) 1 d D U P C 2
O9A O 0.3219(19) 0.3391(18) 0.8198(10) 0.091(9) Uani 0.475(13) 1 d D U 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 Au1 3.0861(7) 4_556 y
Au1 S1 2.336(2) . y
Au1 P1 2.274(2) . y
S1 C1 1.725(10) . ?
S2 C3 1.757(10) . ?
S2 C5 1.753(10) . ?
P1 C18 1.830(6) . ?
P1 C24 1.796(6) . ?
P1 C30 1.815(6) . ?
N1 C1 1.361(12) . ?
N1 C2 1.473(12) . ?
N1 C5 1.404(11) . ?
N2 C1 1.32(2) . ?
N2 C12 1.432(15) . ?
N3 C5 1.296(17) . ?
N3 C6 1.418(14) . ?
F1 C10 1.292(16) . ?
F2 C16 1.446(13) . ?
C1 N2A 1.322(15) . ?
C2 C3 1.489(14) . ?
C3 C4 1.319(15) . ?
C5 N3A 1.29(2) . ?
C6 C7 1.3900 . ?
C6 C11 1.3900 . ?
C7 C8 1.3900 . ?
C8 C9 1.3900 . ?
C9 C10 1.3900 . ?
C10 C11 1.3900 . ?
C16 C15 1.3900 . ?
C16 C17 1.3900 . ?
C15 C14 1.3900 . ?
C14 C13 1.3900 . ?
C13 C12 1.3900 . ?
C12 C17 1.3900 . ?
C18 C19 1.3900 . ?
C18 C23 1.3900 . ?
C19 C20 1.3900 . ?
C20 C21 1.3900 . ?
C21 C22 1.3900 . ?
C22 C23 1.3900 . ?
C24 C25 1.3900 . ?
C24 C29 1.3900 . ?
C25 C26 1.3900 . ?
C26 C27 1.3900 . ?
C27 C28 1.3900 . ?
C28 C29 1.3900 . ?
C30 C31 1.3900 . ?
C30 C35 1.3900 . ?
C31 C32 1.3900 . ?
C32 C33 1.3900 . ?
C33 C34 1.3900 . ?
C34 C35 1.3900 . ?
F1A C10A 1.30(3) . ?
C6A C7A 1.38(2) . ?
C6A C11A 1.38(2) . ?
C6A N3A 1.43(2) . ?
C7A C8A 1.38(2) . ?
C8A C9A 1.39(2) . ?
C9A C10A 1.38(2) . ?
C10A C11A 1.37(2) . ?
F2A C16A 1.475(18) . ?
C12A C13A 1.3900 . ?
C12A C17A 1.3900 . ?
C12A N2A 1.435(13) . ?
C13A C14A 1.3900 . ?
C14A C15A 1.3900 . ?
C15A C16A 1.3900 . ?
C16A C17A 1.3900 . ?
C1A F3 1.291(16) . ?
C1A F4 1.317(16) . ?
C1A F5 1.315(16) . ?
C1A S6 1.793(18) . ?
S6 O7 1.452(15) . ?
S6 O8 1.408(15) . ?
S6 O9 1.410(14) . ?
F4A C1B 1.319(19) . ?
C1B F3A 1.29(2) . ?
C1B F5A 1.28(2) . ?
C1B S6A 1.79(2) . ?
S6A O7A 1.427(17) . ?
S6A O8A 1.389(18) . ?
S6A O9A 1.400(16) . ?

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
S1 Au1 Au1 77.33(7) . 4_556 y
P1 Au1 Au1 102.62(7) . 4_556 y
P1 Au1 S1 175.34(9) . . y
C1 S1 Au1 106.3(4) . . ?
C5 S2 C3 92.5(5) . . ?
C18 P1 Au1 114.4(3) . . ?
C24 P1 Au1 109.2(3) . . ?
C24 P1 C18 109.0(4) . . ?
C24 P1 C30 104.2(4) . . ?
C30 P1 Au1 114.5(3) . . ?
C30 P1 C18 105.0(4) . . ?
C1 N1 C2 121.0(8) . . ?
C1 N1 C5 124.7(9) . . ?
C5 N1 C2 114.0(8) . . ?
C1 N2 C12 133.0(16) . . ?
C5 N3 C6 119.5(14) . . ?
N1 C1 S1 116.9(8) . . ?
N2 C1 S1 123.7(9) . . ?
N2 C1 N1 118.6(11) . . ?
N2A C1 S1 124.9(9) . . ?
N2A C1 N1 118.1(10) . . ?
N1 C2 C3 108.2(8) . . ?
C2 C3 S2 110.9(7) . . ?
C4 C3 S2 123.8(8) . . ?
C4 C3 C2 125.3(9) . . ?
N1 C5 S2 112.0(7) . . ?
N3 C5 S2 127.3(10) . . ?
N3 C5 N1 119.6(11) . . ?
N3A C5 S2 122.9(14) . . ?
N3A C5 N1 123.8(16) . . ?
C7 C6 N3 120.8(11) . . ?
C7 C6 C11 120.0 . . ?
C11 C6 N3 119.0(11) . . ?
C6 C7 C8 120.0 . . ?
C9 C8 C7 120.0 . . ?
C10 C9 C8 120.0 . . ?
F1 C10 C9 119.8(12) . . ?
F1 C10 C11 120.2(12) . . ?
C9 C10 C11 120.0 . . ?
C10 C11 C6 120.0 . . ?
C15 C16 F2 120.01(6) . . ?
C15 C16 C17 120.0 . . ?
C17 C16 F2 119.99(6) . . ?
C16 C15 C14 120.0 . . ?
C13 C14 C15 120.0 . . ?
C14 C13 C12 120.0 . . ?
C13 C12 N2 127.7(18) . . ?
C17 C12 N2 112.3(18) . . ?
C17 C12 C13 120.0 . . ?
C12 C17 C16 120.0 . . ?
C19 C18 P1 121.3(5) . . ?
C19 C18 C23 120.0 . . ?
C23 C18 P1 118.7(5) . . ?
C18 C19 C20 120.0 . . ?
C21 C20 C19 120.0 . . ?
C22 C21 C20 120.0 . . ?
C21 C22 C23 120.0 . . ?
C22 C23 C18 120.0 . . ?
C25 C24 P1 117.2(4) . . ?
C25 C24 C29 120.0 . . ?
C29 C24 P1 122.6(4) . . ?
C24 C25 C26 120.0 . . ?
C27 C26 C25 120.0 . . ?
C26 C27 C28 120.0 . . ?
C29 C28 C27 120.0 . . ?
C28 C29 C24 120.0 . . ?
C31 C30 P1 118.1(4) . . ?
C31 C30 C35 120.0 . . ?
C35 C30 P1 121.9(4) . . ?
C30 C31 C32 120.0 . . ?
C33 C32 C31 120.0 . . ?
C32 C33 C34 120.0 . . ?
C35 C34 C33 120.0 . . ?
C34 C35 C30 120.0 . . ?
C7A C6A C11A 121(2) . . ?
C7A C6A N3A 118(2) . . ?
C11A C6A N3A 121(2) . . ?
C8A C7A C6A 119(2) . . ?
C7A C8A C9A 121(2) . . ?
C10A C9A C8A 120(2) . . ?
F1A C10A C9A 120(2) . . ?
F1A C10A C11A 120(3) . . ?
C11A C10A C9A 120(2) . . ?
C10A C11A C6A 120(2) . . ?
C5 N3A C6A 123(3) . . ?
C13A C12A C17A 120.0 . . ?
C13A C12A N2A 125.5(11) . . ?
C17A C12A N2A 114.4(11) . . ?
C14A C13A C12A 120.0 . . ?
C13A C14A C15A 120.0 . . ?
C16A C15A C14A 120.0 . . ?
C15A C16A F2A 119.88(8) . . ?
C15A C16A C17A 120.0 . . ?
C17A C16A F2A 119.86(9) . . ?
C16A C17A C12A 120.0 . . ?
C1 N2A C12A 127.1(12) . . ?
F3 C1A F4 107(2) . . ?
F3 C1A F5 107.1(19) . . ?
F3 C1A S6 113.7(17) . . ?
F4 C1A S6 104.7(16) . . ?
F5 C1A F4 114(2) . . ?
F5 C1A S6 109.9(15) . . ?
O7 S6 C1A 104.8(12) . . ?
O8 S6 C1A 105.3(16) . . ?
O8 S6 O7 106.5(17) . . ?
O8 S6 O9 119.2(19) . . ?
O9 S6 C1A 104.9(13) . . ?
O9 S6 O7 114.7(16) . . ?
F4A C1B S6A 107.9(18) . . ?
F3A C1B F4A 105(2) . . ?
F3A C1B S6A 115.1(18) . . ?
F5A C1B F4A 103(2) . . ?
F5A C1B F3A 109(2) . . ?
F5A C1B S6A 115.1(17) . . ?
O7A S6A C1B 103.3(14) . . ?
O8A S6A C1B 104.4(16) . . ?
O8A S6A O7A 118(2) . . ?
O8A S6A O9A 111(2) . . ?
O9A S6A C1B 105.0(13) . . ?
O9A S6A O7A 112.9(17) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_c558
_database_code_depnum_ccdc_archive 'CCDC 2234528'
loop_
_audit_author_name
_audit_author_address
'M. Concepcion Gimeno'
;Instituto de Sintesis Quimica y Catalisis Homogenea
Spain
;
_audit_update_record             
;
2023-01-05 deposited with the CCDC.	2023-02-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H19 Au F5 N3 S2'
_chemical_formula_weight         717.52

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   14.8378(2)
_cell_length_b                   12.77496(15)
_cell_length_c                   14.0307(2)
_cell_angle_alpha                90
_cell_angle_beta                 115.4153(19)
_cell_angle_gamma                90
_cell_volume                     2402.16(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    27385
_cell_measurement_theta_min      3.4240
_cell_measurement_theta_max      28.9280

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.984
_exptl_crystal_F_000             1384
_exptl_transmission_factor_min   0.576
_exptl_transmission_factor_max   3.001
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    6.358
_shelx_estimated_absorpt_T_min   0.166
_shelx_estimated_absorpt_T_max   0.516
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.21062
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41r (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 16.0655
_diffrn_reflns_number            64899
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.215
_diffrn_reflns_theta_max         28.929
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6047
_reflns_number_gt                5650
_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       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_structure_solution    SHELXS
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0231P)²+1.7691P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   diffmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6047
_refine_ls_number_parameters     329
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0223
_refine_ls_R_factor_gt           0.0195
_refine_ls_wR_factor_ref         0.0461
_refine_ls_wR_factor_gt          0.0451
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_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 0.25042(2) 0.55262(2) 0.43398(2) 0.01687(4) Uani 1 1 d . . . . .
S1 S 0.12431(5) 0.59319(4) 0.48239(5) 0.02401(13) Uani 1 1 d . . . . .
S2 S -0.19354(4) 0.82465(4) 0.31984(4) 0.01935(11) Uani 1 1 d . . . . .
N1 N -0.01705(13) 0.73685(14) 0.40336(14) 0.0152(4) Uani 1 1 d . . . . .
N2 N -0.01605(14) 0.92087(14) 0.38228(14) 0.0157(4) Uani 1 1 d . . . . .
N3 N 0.14274(14) 0.80049(15) 0.45753(16) 0.0206(4) Uani 1 1 d . . . . .
F1 F 0.37464(11) 0.34034(11) 0.47528(12) 0.0264(3) Uani 1 1 d . . . . .
F2 F 0.51711(11) 0.27798(11) 0.41785(13) 0.0330(3) Uani 1 1 d . . . . .
F3 F 0.57932(11) 0.40595(13) 0.30442(12) 0.0330(3) Uani 1 1 d . . . . .
F4 F 0.49802(11) 0.60129(13) 0.24985(12) 0.0316(3) Uani 1 1 d . . . . .
F5 F 0.35465(11) 0.66421(11) 0.30369(12) 0.0302(3) Uani 1 1 d . . . . .
C1 C 0.35796(16) 0.50519(18) 0.39173(17) 0.0177(4) Uani 1 1 d . . . . .
C2 C 0.40228(17) 0.40733(18) 0.41768(18) 0.0194(4) Uani 1 1 d . . . . .
C3 C 0.47543(17) 0.37326(18) 0.38946(19) 0.0219(5) Uani 1 1 d . . . . .
C4 C 0.50786(18) 0.43844(19) 0.33250(19) 0.0233(5) Uani 1 1 d . . . . .
C5 C 0.46704(18) 0.53672(19) 0.30534(19) 0.0223(5) Uani 1 1 d . . . . .
C6 C 0.39362(18) 0.56696(18) 0.33486(19) 0.0213(5) Uani 1 1 d . . . . .
C7 C 0.08366(17) 0.71986(17) 0.44481(17) 0.0171(4) Uani 1 1 d . . . . .
C8 C -0.08640(17) 0.64767(17) 0.37969(18) 0.0200(5) Uani 1 1 d . . . . .
H8A H -0.066705 0.601901 0.442374 0.024 Uiso 1 1 calc R U . . .
H8B H -0.085161 0.605762 0.320909 0.024 Uiso 1 1 calc R U . . .
C9 C -0.18880(17) 0.69096(18) 0.34969(18) 0.0205(5) Uani 1 1 d . . . . .
C10 C -0.2670(2) 0.6380(2) 0.3449(2) 0.0357(7) Uani 1 1 d . . . . .
H10A H -0.261052 0.565413 0.361306 0.043 Uiso 1 1 calc R U . . .
H10B H -0.329248 0.672353 0.324917 0.043 Uiso 1 1 calc R U . . .
C11 C -0.06276(16) 0.83586(17) 0.37366(16) 0.0149(4) Uani 1 1 d . . . . .
C12 C -0.07902(16) 1.01442(17) 0.34783(18) 0.0181(4) Uani 1 1 d . . . . .
H12A H -0.115137 1.022413 0.392562 0.022 Uiso 1 1 calc R U . . .
H12B H -0.129511 1.003322 0.274411 0.022 Uiso 1 1 calc R U . . .
C13 C -0.02434(17) 1.11483(16) 0.35199(16) 0.0163(4) Uani 1 1 d . . . . .
C14 C 0.07782(17) 1.12138(18) 0.38649(17) 0.0202(5) Uani 1 1 d . . . . .
H14 H 0.117345 1.059742 0.407627 0.024 Uiso 1 1 calc R U . . .
C15 C 0.12343(18) 1.21807(19) 0.39052(18) 0.0238(5) Uani 1 1 d . . . . .
H15 H 0.193751 1.221981 0.414708 0.029 Uiso 1 1 calc R U . . .
C16 C 0.0663(2) 1.30812(18) 0.35931(18) 0.0239(5) Uani 1 1 d . . . . .
H16 H 0.097303 1.373854 0.362242 0.029 Uiso 1 1 calc R U . . .
C17 C -0.0361(2) 1.30218(18) 0.32386(19) 0.0250(5) Uani 1 1 d . . . . .
H17 H -0.075493 1.363870 0.302254 0.030 Uiso 1 1 calc R U . . .
C18 C -0.08144(18) 1.20598(18) 0.31980(18) 0.0212(5) Uani 1 1 d . . . . .
H18 H -0.151852 1.202238 0.294914 0.025 Uiso 1 1 calc R U . . .
C19 C 0.25236(18) 0.7984(2) 0.5109(3) 0.0355(7) Uani 1 1 d . . . . .
H19A H 0.277420 0.738165 0.484873 0.043 Uiso 1 1 calc R U . . .
H19B H 0.274533 0.789442 0.587800 0.043 Uiso 1 1 calc R U . . .
C20 C 0.29471(16) 0.89824(17) 0.49049(19) 0.0204(5) Uani 1 1 d . . . . .
C21 C 0.3233(2) 0.9049(2) 0.4099(2) 0.0373(7) Uani 1 1 d . . . . .
H21 H 0.314135 0.846751 0.364478 0.045 Uiso 1 1 calc R U . . .
C22 C 0.3656(3) 0.9966(3) 0.3947(3) 0.0511(9) Uani 1 1 d . . . . .
H22 H 0.385650 1.000941 0.338963 0.061 Uiso 1 1 calc R U . . .
C23 C 0.3786(2) 1.0809(2) 0.4599(3) 0.0462(8) Uani 1 1 d . . . . .
H23 H 0.407851 1.143409 0.449445 0.055 Uiso 1 1 calc R U . . .
C24 C 0.3495(2) 1.0750(2) 0.5396(2) 0.0336(6) Uani 1 1 d . . . . .
H24 H 0.358169 1.133633 0.584390 0.040 Uiso 1 1 calc R U . . .
C25 C 0.30775(18) 0.9843(2) 0.55546(19) 0.0238(5) Uani 1 1 d . . . . .
H25 H 0.287687 0.980646 0.611208 0.029 Uiso 1 1 calc R U . . .
H3 H 0.110(3) 0.856(3) 0.436(3) 0.050(10) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Au1 C1 2.019(2) . ?
Au1 S1 2.3069(6) . ?
S1 C7 1.728(2) . ?
S2 C9 1.753(2) . ?
S2 C11 1.760(2) . ?
N1 C7 1.368(3) . ?
N1 C11 1.411(3) . ?
N1 C8 1.474(3) . ?
N2 C11 1.266(3) . ?
N2 C12 1.465(3) . ?
N3 C7 1.314(3) . ?
N3 C19 1.470(3) . ?
F1 C2 1.356(3) . ?
F2 C3 1.346(3) . ?
F3 C4 1.345(3) . ?
F4 C5 1.344(3) . ?
F5 C6 1.361(3) . ?
C1 C6 1.379(3) . ?
C1 C2 1.386(3) . ?
C2 C3 1.376(3) . ?
C3 C4 1.376(3) . ?
C4 C5 1.375(3) . ?
C5 C6 1.376(4) . ?
C8 C9 1.498(3) . ?
C9 C10 1.320(3) . ?
C12 C13 1.505(3) . ?
C13 C14 1.382(3) . ?
C13 C18 1.396(3) . ?
C14 C15 1.398(3) . ?
C15 C16 1.384(3) . ?
C16 C17 1.383(4) . ?
C17 C18 1.390(3) . ?
C19 C20 1.503(3) . ?
C20 C21 1.370(4) . ?
C20 C25 1.388(3) . ?
C21 C22 1.388(5) . ?
C22 C23 1.372(5) . ?
C23 C24 1.363(5) . ?
C24 C25 1.376(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Au1 S1 175.51(6) . . ?
C7 S1 Au1 109.97(8) . . ?
C9 S2 C11 93.04(11) . . ?
C7 N1 C11 124.51(18) . . ?
C7 N1 C8 120.16(18) . . ?
C11 N1 C8 115.19(17) . . ?
C11 N2 C12 115.01(19) . . ?
C7 N3 C19 125.6(2) . . ?
C6 C1 C2 114.3(2) . . ?
C6 C1 Au1 123.09(17) . . ?
C2 C1 Au1 122.62(17) . . ?
F1 C2 C3 116.7(2) . . ?
F1 C2 C1 119.7(2) . . ?
C3 C2 C1 123.6(2) . . ?
F2 C3 C2 121.3(2) . . ?
F2 C3 C4 119.2(2) . . ?
C2 C3 C4 119.4(2) . . ?
F3 C4 C5 120.6(2) . . ?
F3 C4 C3 120.0(2) . . ?
C5 C4 C3 119.4(2) . . ?
F4 C5 C4 120.1(2) . . ?
F4 C5 C6 120.9(2) . . ?
C4 C5 C6 119.0(2) . . ?
F5 C6 C5 116.2(2) . . ?
F5 C6 C1 119.5(2) . . ?
C5 C6 C1 124.3(2) . . ?
N3 C7 N1 118.46(19) . . ?
N3 C7 S1 124.56(17) . . ?
N1 C7 S1 116.91(16) . . ?
N1 C8 C9 107.68(18) . . ?
C10 C9 C8 126.1(2) . . ?
C10 C9 S2 122.9(2) . . ?
C8 C9 S2 111.03(16) . . ?
N2 C11 N1 124.5(2) . . ?
N2 C11 S2 124.64(17) . . ?
N1 C11 S2 110.82(15) . . ?
N2 C12 C13 115.17(18) . . ?
C14 C13 C18 119.0(2) . . ?
C14 C13 C12 123.86(19) . . ?
C18 C13 C12 117.1(2) . . ?
C13 C14 C15 120.5(2) . . ?
C16 C15 C14 120.1(2) . . ?
C17 C16 C15 119.8(2) . . ?
C16 C17 C18 120.1(2) . . ?
C17 C18 C13 120.5(2) . . ?
N3 C19 C20 110.4(2) . . ?
C21 C20 C25 119.2(2) . . ?
C21 C20 C19 120.9(2) . . ?
C25 C20 C19 119.9(2) . . ?
C20 C21 C22 120.0(3) . . ?
C23 C22 C21 120.2(3) . . ?
C24 C23 C22 120.0(3) . . ?
C23 C24 C25 120.1(3) . . ?
C24 C25 C20 120.4(2) . . ?

_refine_diff_density_max         0.932
_refine_diff_density_min         -1.178
_refine_diff_density_rms         0.094



####################################################################### 
# 
# 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_c456
_database_code_depnum_ccdc_archive 'CCDC 2234525'
loop_
_audit_author_name
_audit_author_address
'M. Concepcion Gimeno'
;Instituto de Sintesis Quimica y Catalisis Homogenea
Spain
;
_audit_update_record             
;
2023-02-17 deposited with the CCDC.	2023-02-22 downloaded from the CCDC.
;
_audit_creation_date             2023-02-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_chemical_formula_moiety         '0.667(C17 H15 N3 S2)'
_chemical_formula_sum            'C11.333 H10 N2 S1.333'
_chemical_formula_weight         216.974
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.86690 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   5.6436(11)
_cell_length_b                   11.400(2)
_cell_length_c                   12.260(3)
_cell_angle_alpha                101.37(3)
_cell_angle_beta                 90.70(3)
_cell_angle_gamma                99.42(3)
_cell_volume                     762.1(3)
_cell_formula_units_Z            3
_cell_measurement_reflns_used    4182
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      0.2290
_cell_measurement_theta_min      4.4180
_exptl_absorpt_coefficient_mu    0.348
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79493
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_description       needle
_exptl_crystal_F_000             340.655
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_Laue_measured_fraction_full 0.9935
_diffrn_reflns_Laue_measured_fraction_max 0.9238
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16599
_diffrn_reflns_point_group_measured_fraction_full 0.9935
_diffrn_reflns_point_group_measured_fraction_max 0.9238
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         30.78
_diffrn_reflns_theta_min         4.49
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean 16.0655
_diffrn_measured_fraction_theta_full 0.9935
_diffrn_measured_fraction_theta_max 0.9238
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'w rotations'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              15
_reflns_limit_k_min              -16
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                3319
_reflns_number_total             4399
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.4374
_refine_diff_density_min         -0.4132
_refine_diff_density_rms         0.1026
_refine_ls_d_res_high            0.6944
_refine_ls_d_res_low             4.5405
_refine_ls_goodness_of_fit_ref   1.0447
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     259
_refine_ls_number_reflns         4399
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0428
_refine_ls_restrained_S_all      1.0447
_refine_ls_shift/su_max          -0.0006
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0408P)²+0.3193P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0908
_refine_ls_wR_factor_ref         0.1021
_olex2_refinement_description    
;
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
S1 S 0.23072(8) 0.94414(4) 0.81349(4) 0.02614(12) Uani 1.000000 .
S2 S -0.32935(8) 0.56907(4) 0.90123(4) 0.02364(12) Uani 1.000000 .
N2 N -0.0393(2) 0.73279(12) 0.82200(12) 0.0181(3) Uani 1.000000 .
N1 N 0.2650(3) 0.72139(13) 0.69849(12) 0.0192(3) Uani 1.000000 .
N3 N 0.0049(2) 0.52952(12) 0.75034(12) 0.0196(3) Uani 1.000000 .
C12 C 0.5350(3) 0.86017(16) 0.60261(15) 0.0229(4) Uani 1.000000 .
C13 C 0.1549(3) 0.79406(15) 0.77332(14) 0.0183(3) Uani 1.000000 .
C2 C 0.0973(3) 0.34530(15) 0.79819(14) 0.0194(3) Uani 1.000000 .
C7 C 0.4626(3) 0.74874(15) 0.63275(14) 0.0187(3) Uani 1.000000 .
C4 C -0.1843(3) 0.15759(15) 0.75594(15) 0.0204(3) Uani 1.000000 .
C16 C -0.0976(3) 0.60732(14) 0.81318(14) 0.0174(3) Uani 1.000000 .
C1 C -0.0655(3) 0.40385(14) 0.75258(14) 0.0175(3) Uani 1.000000 .
C15 C -0.3758(3) 0.71984(15) 0.94088(14) 0.0200(3) Uani 1.000000 .
C5 C -0.3450(3) 0.21584(16) 0.70953(15) 0.0212(3) Uani 1.000000 .
C6 C -0.2860(3) 0.33842(16) 0.70676(15) 0.0206(3) Uani 1.000000 .
C3 C 0.0371(3) 0.22260(16) 0.79955(15) 0.0212(3) Uani 1.000000 .
C14 C -0.1791(3) 0.80579(16) 0.90166(16) 0.0220(4) Uani 1.000000 .
C8 C 0.5834(3) 0.65204(17) 0.59264(15) 0.0229(4) Uani 1.000000 .
C10 C 0.8537(3) 0.78000(18) 0.49818(15) 0.0274(4) Uani 1.000000 .
C9 C 0.7769(3) 0.66813(18) 0.52595(16) 0.0267(4) Uani 1.000000 .
C11 C 0.7310(3) 0.87446(17) 0.53637(16) 0.0273(4) Uani 1.000000 .
C18 C -0.5589(3) 0.75138(18) 0.99922(15) 0.0245(4) Uani 1.000000 .
H12 H 0.452(4) 0.9236(19) 0.6267(17) 0.026(5) Uiso 1.000000 .
H1 H 0.217(4) 0.644(2) 0.6955(18) 0.030(6) Uiso 1.000000 .
H2 H 0.254(4) 0.3912(19) 0.8290(18) 0.030(5) Uiso 1.000000 .
H14a H -0.077(4) 0.848(2) 0.9656(19) 0.033(6) Uiso 1.000000 .
H9 H 0.858(4) 0.597(2) 0.4985(17) 0.030(6) Uiso 1.000000 .
H14b H -0.240(3) 0.8636(18) 0.8640(17) 0.024(5) Uiso 1.000000 .
H8 H 0.534(4) 0.574(2) 0.6157(17) 0.028(5) Uiso 1.000000 .
H3 H 0.149(4) 0.184(2) 0.8316(18) 0.032(6) Uiso 1.000000 .
H11 H 0.779(4) 0.952(2) 0.5158(19) 0.036(6) Uiso 1.000000 .
H4 H -0.218(3) 0.0751(19) 0.7557(16) 0.021(5) Uiso 1.000000 .
H10 H 0.985(4) 0.791(2) 0.4541(18) 0.032(6) Uiso 1.000000 .
H18a H -0.679(4) 0.693(2) 1.0237(18) 0.034(6) Uiso 1.000000 .
H18b H -0.577(4) 0.835(2) 1.0173(17) 0.027(5) Uiso 1.000000 .
H6 H -0.397(4) 0.3805(19) 0.6737(18) 0.031(6) Uiso 1.000000 .
H5 H -0.492(4) 0.172(2) 0.6787(18) 0.032(6) Uiso 1.000000 .


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
S1 C13 1.6661(17) . ?
S2 C16 1.7605(17) . ?
S2 C15 1.7551(18) . ?
N2 C13 1.405(2) . ?
N2 C16 1.396(2) . ?
N2 C14 1.477(2) . ?
N1 C13 1.340(2) . ?
N1 C7 1.414(2) . ?
N1 H1 0.87(2) . ?
N3 C16 1.274(2) . ?
N3 C1 1.428(2) . ?
C12 C7 1.391(2) . ?
C12 C11 1.388(3) . ?
C12 H12 0.93(2) . ?
C2 C1 1.392(2) . ?
C2 C3 1.388(2) . ?
C2 H2 0.98(2) . ?
C7 C8 1.401(2) . ?
C4 C5 1.386(2) . ?
C4 C3 1.386(2) . ?
C4 H4 0.93(2) . ?
C1 C6 1.391(2) . ?
C15 C14 1.505(2) . ?
C15 C18 1.322(2) . ?
C5 C6 1.390(2) . ?
C5 H5 0.93(2) . ?
C6 H6 0.98(2) . ?
C3 H3 0.95(2) . ?
C14 H14a 0.96(2) . ?
C14 H14b 0.98(2) . ?
C8 C9 1.382(3) . ?
C8 H8 0.98(2) . ?
C10 C9 1.387(3) . ?
C10 C11 1.382(3) . ?
C10 H10 0.93(2) . ?
C9 H9 1.00(2) . ?
C11 H11 0.96(2) . ?
C18 H18a 0.97(2) . ?
C18 H18b 0.96(2) . ?

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
C15 S2 C16 92.86(8) . . ?
C16 N2 C13 126.09(13) . . ?
C14 N2 C13 118.19(13) . . ?
C14 N2 C16 115.24(13) . . ?
C7 N1 C13 130.76(14) . . ?
H1 N1 C13 114.3(14) . . ?
H1 N1 C7 114.5(14) . . ?
C1 N3 C16 118.94(14) . . ?
C11 C12 C7 119.21(17) . . ?
H12 C12 C7 119.8(13) . . ?
H12 C12 C11 121.0(13) . . ?
N2 C13 S1 119.27(12) . . ?
N1 C13 S1 126.49(13) . . ?
N1 C13 N2 114.23(14) . . ?
C3 C2 C1 119.90(16) . . ?
H2 C2 C1 119.7(12) . . ?
H2 C2 C3 120.4(12) . . ?
C12 C7 N1 125.07(15) . . ?
C8 C7 N1 115.36(15) . . ?
C8 C7 C12 119.51(16) . . ?
C3 C4 C5 119.43(16) . . ?
H4 C4 C5 121.7(12) . . ?
H4 C4 C3 118.9(12) . . ?
N2 C16 S2 111.62(11) . . ?
N3 C16 S2 123.78(13) . . ?
N3 C16 N2 124.59(15) . . ?
C2 C1 N3 118.30(14) . . ?
C6 C1 N3 121.91(15) . . ?
C6 C1 C2 119.74(15) . . ?
C14 C15 S2 111.08(12) . . ?
C18 C15 S2 123.32(15) . . ?
C18 C15 C14 125.59(16) . . ?
C6 C5 C4 120.56(16) . . ?
H5 C5 C4 119.8(13) . . ?
H5 C5 C6 119.6(13) . . ?
C5 C6 C1 119.80(16) . . ?
H6 C6 C1 118.7(13) . . ?
H6 C6 C5 121.5(13) . . ?
C4 C3 C2 120.55(16) . . ?
H3 C3 C2 118.8(13) . . ?
H3 C3 C4 120.6(13) . . ?
C15 C14 N2 107.87(13) . . ?
H14a C14 N2 109.3(12) . . ?
H14a C14 C15 107.8(13) . . ?
H14b C14 N2 108.2(12) . . ?
H14b C14 C15 113.0(12) . . ?
H14b C14 H14a 110.6(17) . . ?
C9 C8 C7 120.22(17) . . ?
H8 C8 C7 119.0(12) . . ?
H8 C8 C9 120.7(12) . . ?
C11 C10 C9 119.07(17) . . ?
H10 C10 C9 120.2(13) . . ?
H10 C10 C11 120.7(13) . . ?
C10 C9 C8 120.42(17) . . ?
H9 C9 C8 117.8(12) . . ?
H9 C9 C10 121.7(12) . . ?
C10 C11 C12 121.52(18) . . ?
H11 C11 C12 118.4(13) . . ?
H11 C11 C10 120.1(13) . . ?
H18a C18 C15 122.5(13) . . ?
H18b C18 C15 119.7(12) . . ?
H18b C18 H18a 117.8(17) . . ?

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
S1 C13 N2 C16 -167.48(12) . . . . ?
S1 C13 N2 C14 4.19(16) . . . . ?
S1 C13 N1 C7 -1.9(2) . . . . ?
S2 C16 N2 C13 172.19(11) . . . . ?
S2 C16 N2 C14 0.31(14) . . . . ?
S2 C16 N3 C1 -1.75(17) . . . . ?
S2 C15 C14 N2 11.92(12) . . . . ?
N2 C13 N1 C7 179.62(13) . . . . ?
N2 C16 N3 C1 177.44(16) . . . . ?
N2 C14 C15 C18 -169.18(14) . . . . ?
N1 C7 C12 C11 -179.19(18) . . . . ?
N1 C7 C8 C9 178.94(15) . . . . ?
N3 C1 C2 C3 -178.58(15) . . . . ?
N3 C1 C6 C5 179.07(16) . . . . ?
C12 C7 C8 C9 1.7(2) . . . . ?
C12 C11 C10 C9 0.7(2) . . . . ?
C2 C1 C6 C5 1.74(19) . . . . ?
C2 C3 C4 C5 0.8(2) . . . . ?
C7 C8 C9 C10 0.1(2) . . . . ?
C4 C5 C6 C1 -1.1(2) . . . . ?
C8 C9 C10 C11 -1.2(2) . . . . ?


_olex2_refine_details            
;
Refinement using NoSpherA2, an implementation of
NOn-SPHERical Atom-form-factors in Olex2.
Please cite:
F. Kleemiss et al. Chem. Sci. DOI 10.1039/D0SC05526C - 2021
NoSpherA2 implementation of HAR makes use of
tailor-made aspherical atomic form factors calculated
on-the-fly from a Hirshfeld-partitioned electron density (ED) - not from
spherical-atom form factors.

The ED is calculated from a gaussian basis set single determinant SCF
wavefunction - either Hartree-Fock or DFT using selected funtionals
 - for a fragment of the crystal.
This fragment can be embedded in an electrostatic crystal field by employing cluster charges
or modelled using implicit solvation models, depending on the software used.
The following options were used:
   SOFTWARE:       ORCA 5.0
   PARTITIONING:   NoSpherA2
   INT ACCURACY:   Normal
   METHOD:         R2SCAN
   BASIS SET:      def2-TZVP
   CHARGE:         0
   MULTIPLICITY:   1
   DATE:           2023-01-31_15-48-37
;
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_c537
_database_code_depnum_ccdc_archive 'CCDC 2234524'
loop_
_audit_author_name
_audit_author_address
'M. Concepcion Gimeno'
;Instituto de Sintesis Quimica y Catalisis Homogenea
Spain
;
_audit_update_record             
;
2023-02-17 deposited with the CCDC.	2023-02-22 downloaded from the CCDC.
;
_audit_creation_date             2023-01-31
_audit_creation_method           
;
Olex2 1.5-dev
(compiled 2023.01.20 svn.r024a95a1 for OlexSys, GUI svn.r6444)
;
_chemical_formula_moiety         '2(C10 H9 F N2 S)'
_chemical_formula_sum            'C20 H18 F2 N4 S2'
_chemical_formula_weight         416.522
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.27760 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.86690 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   8.5021(3)
_cell_length_b                   10.7959(4)
_cell_length_c                   11.6276(4)
_cell_angle_alpha                74.821(3)
_cell_angle_beta                 89.867(3)
_cell_angle_gamma                71.907(3)
_cell_volume                     975.46(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6188
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.3850
_cell_measurement_theta_min      3.6370
_exptl_absorpt_coefficient_mu    0.305
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54254
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41r (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_description       prism
_exptl_crystal_F_000             432.761
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.14
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_Laue_measured_fraction_full 0.9963
_diffrn_reflns_Laue_measured_fraction_max 0.9964
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            19886
_diffrn_reflns_point_group_measured_fraction_full 0.9963
_diffrn_reflns_point_group_measured_fraction_max 0.9964
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         3.24
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 16.0655
_diffrn_measured_fraction_theta_full 0.9963
_diffrn_measured_fraction_theta_max 0.9964
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              13
_reflns_limit_k_min              -12
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                3001
_reflns_number_total             3604
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-dev (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-dev (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5-dev (Bourhis et al., 2015)'
_computing_structure_solution    SHELXS
_refine_diff_density_max         0.2757
_refine_diff_density_min         -0.3486
_refine_diff_density_rms         0.0638
_refine_ls_d_res_high            0.8255
_refine_ls_d_res_low             6.2822
_refine_ls_goodness_of_fit_ref   1.0815
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    35
_refine_ls_number_parameters     278
_refine_ls_number_reflns         3604
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0365
_refine_ls_restrained_S_all      1.0815
_refine_ls_shift/su_max          0.0005
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0365P)²+0.4597P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0846
_refine_ls_wR_factor_ref         0.0898
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Others
 Sof(F3)=Sof(F4)=Sof(Hi)=Sof(H17)=1-FVAR(1)
 Sof(F1)=Sof(Hg)=Sof(F2)=Sof(H19)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C3(Hc,Hd), C13(H13a,H13b)
3.b Aromatic/amide H refined with riding coordinates:
 C6(He), C8(Hf), C9(Hg), C10(Hh), C16(H16), C18(H18), C19(H19), C20(H20),
 C7(Hi), C17(H17)
3.c X=CH2 refined with riding coordinates:
 C2(Ha,Hb), C12(H12a,H12b)
;
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_refinement_flags_posn
_atom_site_disorder_group
S1 S 1.22710(6) 0.76942(5) 0.88999(5) 0.03144(15) Uani 1.000000 . .
S2 S 0.26167(6) 1.19222(6) 0.27651(5) 0.03302(15) Uani 1.000000 . .
N1 N 0.92272(18) 0.93116(16) 0.88960(14) 0.0260(4) Uani 1.000000 . .
H H 1.176(3) 0.980(2) 0.7048(19) 0.0312(4) Uiso 1.000000 R .
N2 N 1.07598(19) 0.99966(16) 0.72844(15) 0.0259(4) Uani 1.000000 . .
N3 N 0.57968(18) 1.05351(16) 0.32896(15) 0.0262(4) Uani 1.000000 . .
N4 N 0.43411(19) 0.98517(16) 0.19773(15) 0.0243(4) Uani 1.000000 . .
H4 H 0.340(3) 1.003(2) 0.1668(19) 0.0292(4) Uiso 1.000000 R .
C1 C 1.1187(2) 0.7162(2) 1.01228(18) 0.0287(4) Uani 1.000000 . .
C2 C 1.1823(3) 0.6063(2) 1.1009(2) 0.0414(6) Uani 1.000000 . .
Ha H 1.2934(3) 0.5501(2) 1.1014(2) 0.0497(7) Uiso 1.000000 R .
Hb H 1.1172(3) 0.5831(2) 1.1644(2) 0.0497(7) Uiso 1.000000 R .
C3 C 0.9458(2) 0.8187(2) 0.99736(18) 0.0312(5) Uani 1.000000 . .
Hc H 0.9279(2) 0.8544(2) 1.06821(18) 0.0374(6) Uiso 1.000000 R .
Hd H 0.8622(2) 0.7732(2) 0.99253(18) 0.0374(6) Uiso 1.000000 R .
C4 C 1.0525(2) 0.91711(19) 0.83240(17) 0.0228(4) Uani 1.000000 . .
C5 C 0.9611(2) 1.11716(18) 0.65429(18) 0.0238(4) Uani 1.000000 . .
C6 C 0.8210(2) 1.19624(19) 0.69401(19) 0.0272(4) Uani 1.000000 . .
He H 0.7957(2) 1.17181(19) 0.77479(19) 0.0327(5) Uiso 1.000000 R .
C7 C 0.7200(2) 1.3110(2) 0.6127(2) 0.0317(5) Uani 1.000000 . .
C8 C 0.7506(2) 1.3524(2) 0.4953(2) 0.0314(5) Uani 1.000000 . .
Hf H 0.6779(2) 1.4323(2) 0.4419(2) 0.0377(6) Uiso 1.000000 R .
C9 C 0.8914(2) 1.2732(2) 0.4580(2) 0.0308(5) Uani 1.000000 . .
Hg H 0.9170(2) 1.2998(2) 0.3775(2) 0.0369(6) Uiso 0.763(3) R 1
C10 C 0.9956(2) 1.15625(19) 0.53541(17) 0.0262(4) Uani 1.000000 . .
Hh H 1.0908(2) 1.10231(19) 0.50773(17) 0.0314(5) Uiso 1.000000 R .
C11 C 0.3691(2) 1.2451(2) 0.37355(17) 0.0273(4) Uani 1.000000 . .
C12 C 0.3013(3) 1.3461(2) 0.42001(19) 0.0337(5) Uani 1.000000 . .
H12a H 0.1865(3) 1.3962(2) 0.40174(19) 0.0404(6) Uiso 1.000000 R .
H12b H 0.3671(3) 1.3690(2) 0.47184(19) 0.0404(6) Uiso 1.000000 R .
C13 C 0.5480(2) 1.1542(2) 0.3961(2) 0.0370(5) Uani 1.000000 . .
H13a H 0.5738(2) 1.1076(2) 0.4826(2) 0.0444(6) Uiso 1.000000 R .
H13b H 0.6219(2) 1.2100(2) 0.3724(2) 0.0444(6) Uiso 1.000000 R .
C14 C 0.4488(2) 1.06279(19) 0.26881(17) 0.0228(4) Uani 1.000000 . .
C15 C 0.5462(2) 0.86137(19) 0.19061(17) 0.0239(4) Uani 1.000000 . .
C16 C 0.6849(2) 0.78690(19) 0.27194(18) 0.0258(4) Uani 1.000000 . .
H16 H 0.7142(2) 0.82139(19) 0.33303(18) 0.0309(5) Uiso 1.000000 R .
C17 C 0.7777(2) 0.6618(2) 0.2606(2) 0.0321(5) Uani 1.000000 . .
C18 C 0.7432(3) 0.6057(2) 0.1747(2) 0.0344(5) Uani 1.000000 . .
H18 H 0.8098(3) 0.5184(2) 0.1708(2) 0.0412(6) Uiso 1.000000 R .
C19 C 0.6064(3) 0.6826(2) 0.0940(2) 0.0343(5) Uani 1.000000 . .
H19 H 0.5789(3) 0.6474(2) 0.0328(2) 0.0411(6) Uiso 0.763(3) R 1
C20 C 0.5093(2) 0.8090(2) 0.10036(18) 0.0288(4) Uani 1.000000 . .
H20 H 0.4171(2) 0.8603(2) 0.04320(18) 0.0345(5) Uiso 1.000000 R .
F2 F 0.91033(17) 0.58938(14) 0.33692(13) 0.0320(4) Uani 0.763(3) . 1
F1 F 0.58346(17) 1.38732(15) 0.64610(14) 0.0355(5) Uani 0.763(3) . 1
F3 F 0.9038(6) 1.3103(5) 0.3548(4) 0.0281(14) Uani 0.237(3) . 2
F4 F 0.5824(7) 0.6159(6) 0.0303(6) 0.0523(18) Uani 0.237(3) . 2
Hi H 0.6236(2) 1.3646(2) 0.6395(2) 0.0381(6) Uiso 0.237(3) R 2
H17 H 0.8719(2) 0.6109(2) 0.3160(2) 0.0385(6) Uiso 0.237(3) R 2


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
S1 C1 1.760(2) . ?
S1 C4 1.7804(18) . ?
S2 C11 1.760(2) . ?
S2 C14 1.7822(18) . ?
N1 C3 1.463(3) . ?
N1 C4 1.276(2) . ?
N2 C4 1.357(2) . ?
N2 C5 1.403(2) . ?
N3 C13 1.458(3) . ?
N3 C14 1.279(2) . ?
N4 C14 1.353(2) . ?
N4 C15 1.403(2) . ?
C1 C2 1.314(3) . ?
C1 C3 1.519(3) . ?
C5 C6 1.391(3) . ?
C5 C10 1.394(3) . ?
C6 C7 1.376(3) . ?
C7 C8 1.372(3) . ?
C7 F1 1.322(2) . ?
C8 C9 1.382(3) . ?
C9 C10 1.380(3) . ?
C9 F3 1.176(5) . ?
C11 C12 1.316(3) . ?
C11 C13 1.512(3) . ?
C15 C16 1.396(3) . ?
C15 C20 1.394(3) . ?
C16 C17 1.377(3) . ?
C17 C18 1.370(3) . ?
C17 F2 1.328(2) . ?
C18 C19 1.386(3) . ?
C19 C20 1.379(3) . ?
C19 F4 1.217(6) . ?

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
C4 S1 C1 90.01(9) . . ?
C14 S2 C11 89.66(9) . . ?
C4 N1 C3 111.81(16) . . ?
C5 N2 C4 128.53(16) . . ?
C14 N3 C13 112.11(16) . . ?
C15 N4 C14 128.41(16) . . ?
C2 C1 S1 124.07(16) . . ?
C3 C1 S1 108.58(14) . . ?
C3 C1 C2 127.34(19) . . ?
C1 C3 N1 111.49(15) . . ?
N1 C4 S1 118.06(15) . . ?
N2 C4 S1 113.54(13) . . ?
N2 C4 N1 128.37(17) . . ?
C6 C5 N2 123.69(18) . . ?
C10 C5 N2 116.62(16) . . ?
C10 C5 C6 119.66(18) . . ?
C7 C6 C5 117.99(19) . . ?
C8 C7 C6 123.78(18) . . ?
F1 C7 C6 119.9(2) . . ?
F1 C7 C8 116.27(19) . . ?
C9 C8 C7 117.32(19) . . ?
C10 C9 C8 121.2(2) . . ?
F3 C9 C8 113.4(3) . . ?
F3 C9 C10 125.2(3) . . ?
C9 C10 C5 120.03(18) . . ?
C12 C11 S2 124.61(16) . . ?
C13 C11 S2 109.09(14) . . ?
C13 C11 C12 126.29(19) . . ?
C11 C13 N3 111.27(16) . . ?
N3 C14 S2 117.85(14) . . ?
N4 C14 S2 114.64(13) . . ?
N4 C14 N3 127.52(17) . . ?
C16 C15 N4 123.50(17) . . ?
C20 C15 N4 116.89(17) . . ?
C20 C15 C16 119.53(18) . . ?
C17 C16 C15 117.74(19) . . ?
C18 C17 C16 124.38(19) . . ?
F2 C17 C16 118.7(2) . . ?
F2 C17 C18 116.92(18) . . ?
C19 C18 C17 116.74(19) . . ?
C20 C19 C18 121.6(2) . . ?
F4 C19 C18 109.4(3) . . ?
F4 C19 C20 128.6(3) . . ?
C19 C20 C15 120.03(19) . . ?


_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_c547
_database_code_depnum_ccdc_archive 'CCDC 2234526'
loop_
_audit_author_name
_audit_author_address
'M. Concepcion Gimeno'
;Instituto de Sintesis Quimica y Catalisis Homogenea
Spain
;
_audit_update_record             
;
2023-02-17 deposited with the CCDC.	2023-02-22 downloaded from the CCDC.
;
_audit_creation_date             2023-01-31
_audit_creation_method           
;
Olex2 1.5-dev
(compiled 2023.01.20 svn.r024a95a1 for OlexSys, GUI svn.r6444)
;
_chemical_formula_moiety         'C17 H13 F2 N3 S2'
_chemical_formula_sum            'C17 H13 F2 N3 S2'
_chemical_formula_weight         361.442
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.27760 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.86690 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   7.2678(2)
_cell_length_b                   10.3032(3)
_cell_length_c                   11.8115(4)
_cell_angle_alpha                66.050(3)
_cell_angle_beta                 75.680(3)
_cell_angle_gamma                86.964(2)
_cell_volume                     782.08(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9680
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.0250
_cell_measurement_theta_min      3.5110
_exptl_absorpt_coefficient_mu    0.366
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84573
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41r (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_description       prism
_exptl_crystal_F_000             372.727
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 0.9958
_diffrn_reflns_Laue_measured_fraction_max 0.9312
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            21492
_diffrn_reflns_point_group_measured_fraction_full 0.9958
_diffrn_reflns_point_group_measured_fraction_max 0.9312
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         31.06
_diffrn_reflns_theta_min         3.37
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 16.0655
_diffrn_measured_fraction_theta_full 0.9958
_diffrn_measured_fraction_theta_max 0.9312
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω rotations'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -9
_reflns_limit_k_max              14
_reflns_limit_k_min              -13
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                4196
_reflns_number_total             4667
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-dev (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-dev (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5-dev (Bourhis et al., 2015)'
_computing_structure_solution    SHELXS
_refine_diff_density_max         0.4661
_refine_diff_density_min         -0.2702
_refine_diff_density_rms         0.0662
_refine_ls_d_res_high            0.6888
_refine_ls_d_res_low             6.0512
_refine_ls_goodness_of_fit_ref   1.0443
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    27
_refine_ls_number_parameters     227
_refine_ls_number_reflns         4667
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0323
_refine_ls_restrained_S_all      1.0418
_refine_ls_shift/su_max          0.0010
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0428P)²+0.3772P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0838
_refine_ls_wR_factor_ref         0.0878
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Rigid body (RIGU) restrains
 C4, F3, C6, C5, F1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Sof(F3)=Sof(H6)=1-FVAR(1)
 Sof(F1)=Sof(H4)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C8(H8a,H8b)
4.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C5(H5), C3(H3), C17(H17), C16(H16), C15(H15), C13(H13), C4(H4),
 C6(H6), N1(H1)
4.c X=CH2 refined with riding coordinates:
 C10(H10a,H10b)
;
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_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_disorder_group
S1 S 0.11454(5) 0.71915(3) 0.58345(3) 0.01975(8) Uani 1.000000 . . .
S2 S 0.18157(4) 0.93987(3) 0.09287(3) 0.01713(8) Uani 1.000000 . . .
N1 N 0.23065(14) 0.55766(10) 0.45008(9) 0.01485(18) Uani 1.000000 . . .
N2 N 0.16420(13) 0.78891(10) 0.33544(9) 0.01348(18) Uani 1.000000 . . .
N3 N 0.26410(14) 0.66406(10) 0.20455(9) 0.01479(18) Uani 1.000000 . . .
C1 C 0.17356(15) 0.68175(12) 0.45482(10) 0.0138(2) Uani 1.000000 . . .
C2 C 0.26643(15) 0.42855(12) 0.54466(11) 0.0142(2) Uani 1.000000 . . .
C3 C 0.33072(17) 0.32246(13) 0.50099(11) 0.0174(2) Uani 1.000000 . . .
C4 C 0.37466(18) 0.19181(13) 0.58417(12) 0.0204(2) Uani 1.000000 . U .
C5 C 0.35551(17) 0.16254(13) 0.71238(12) 0.0201(2) Uani 1.000000 . U .
C6 C 0.29063(17) 0.26852(13) 0.75192(11) 0.0185(2) Uani 1.000000 . U .
C7 C 0.24459(17) 0.40089(12) 0.67331(11) 0.0168(2) Uani 1.000000 . . .
C8 C 0.10548(17) 0.92989(12) 0.33090(11) 0.0160(2) Uani 1.000000 . . .
C9 C 0.08104(16) 1.01865(12) 0.19902(11) 0.0154(2) Uani 1.000000 . . .
C10 C -0.00205(18) 1.14152(13) 0.16446(12) 0.0208(2) Uani 1.000000 . . .
C11 C 0.21086(15) 0.77844(11) 0.21775(10) 0.01291(19) Uani 1.000000 . . .
C12 C 0.30051(16) 0.65484(12) 0.08472(11) 0.0137(2) Uani 1.000000 . . .
C13 C 0.42200(16) 0.75217(12) -0.02602(11) 0.0155(2) Uani 1.000000 . . .
C14 C 0.44795(16) 0.73083(13) -0.13674(11) 0.0175(2) Uani 1.000000 . . .
C15 C 0.36462(17) 0.61808(13) -0.14363(12) 0.0183(2) Uani 1.000000 . . .
C16 C 0.24823(17) 0.52058(13) -0.03179(12) 0.0183(2) Uani 1.000000 . . .
C17 C 0.21596(16) 0.53826(12) 0.08184(11) 0.0167(2) Uani 1.000000 . . .
F1 F 0.26749(14) 0.24367(9) 0.87608(8) 0.0253(3) Uani 0.876(3) . U 1
F2 F 0.56335(12) 0.82571(9) -0.24527(7) 0.02849(19) Uani 1.000000 . . .
F3 F 0.4182(10) 0.0843(6) 0.5492(6) 0.0276(19) Uani 0.124(3) . U 2
H7 H 0.19972(17) 0.47049(12) 0.70566(11) 0.0202(3) Uiso 1.000000 R . .
H5 H 0.38593(17) 0.07327(13) 0.76998(12) 0.0242(3) Uiso 1.000000 R . .
H3 H 0.34421(17) 0.34032(13) 0.41378(11) 0.0209(3) Uiso 1.000000 R . .
H17 H 0.13616(16) 0.47081(12) 0.15773(11) 0.0201(3) Uiso 1.000000 R . .
H16 H 0.19006(17) 0.44092(13) -0.03307(12) 0.0220(3) Uiso 1.000000 R . .
H15 H 0.38598(17) 0.60741(13) -0.22199(12) 0.0220(3) Uiso 1.000000 R . .
H13 H 0.48448(16) 0.83025(12) -0.02503(11) 0.0186(2) Uiso 1.000000 R . .
H4 H 0.41861(18) 0.12100(13) 0.55318(12) 0.0244(3) Uiso 0.876(3) R . 1
H6 H 0.27637(17) 0.24961(13) 0.83942(11) 0.0223(3) Uiso 0.124(3) R . 2
H8a H -0.01569(17) 0.91991(12) 0.39536(11) 0.0192(3) Uiso 1.000000 R . .
H8b H 0.20352(17) 0.97575(12) 0.34976(11) 0.0192(3) Uiso 1.000000 R . .
H1 H 0.24916(14) 0.55673(10) 0.37392(9) 0.0178(2) Uiso 1.000000 R . .
H10a H -0.00936(18) 1.19157(13) 0.07829(12) 0.0250(3) Uiso 1.000000 R . .
H10b H -0.05432(18) 1.17956(13) 0.22585(12) 0.0250(3) Uiso 1.000000 R . .


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
S1 C1 1.6663(12) . ?
S2 C9 1.7537(12) . ?
S2 C11 1.7645(11) . ?
N1 C1 1.3418(14) . ?
N1 C2 1.4091(14) . ?
N2 C1 1.4097(14) . ?
N2 C8 1.4756(14) . ?
N2 C11 1.3942(14) . ?
N3 C11 1.2781(14) . ?
N3 C12 1.4156(14) . ?
C2 C3 1.4014(16) . ?
C2 C7 1.3962(15) . ?
C3 C4 1.3839(17) . ?
C4 C5 1.3903(18) . ?
C4 F3 1.329(6) . ?
C5 C6 1.3723(18) . ?
C6 C7 1.3825(16) . ?
C6 F1 1.3498(14) . ?
C8 C9 1.5024(16) . ?
C9 C10 1.3248(16) . ?
C12 C13 1.3977(16) . ?
C12 C17 1.3940(16) . ?
C13 C14 1.3788(16) . ?
C14 C15 1.3780(17) . ?
C14 F2 1.3565(13) . ?
C15 C16 1.3891(17) . ?
C16 C17 1.3885(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 S2 C9 92.66(5) . . ?
C2 N1 C1 131.82(10) . . ?
C8 N2 C1 117.87(9) . . ?
C11 N2 C1 126.97(9) . . ?
C11 N2 C8 115.12(9) . . ?
C12 N3 C11 121.82(10) . . ?
N1 C1 S1 127.26(9) . . ?
N2 C1 S1 118.75(8) . . ?
N2 C1 N1 113.99(10) . . ?
C3 C2 N1 114.86(10) . . ?
C7 C2 N1 125.65(10) . . ?
C7 C2 C3 119.49(10) . . ?
C4 C3 C2 120.38(11) . . ?
C5 C4 C3 121.04(12) . . ?
F3 C4 C3 121.9(3) . . ?
F3 C4 C5 116.7(3) . . ?
C6 C5 C4 116.94(11) . . ?
C7 C6 C5 124.57(11) . . ?
F1 C6 C5 118.80(11) . . ?
F1 C6 C7 116.63(11) . . ?
C6 C7 C2 117.58(11) . . ?
C9 C8 N2 107.91(9) . . ?
C8 C9 S2 111.03(8) . . ?
C10 C9 S2 123.38(10) . . ?
C10 C9 C8 125.59(11) . . ?
N2 C11 S2 111.60(8) . . ?
N3 C11 S2 125.13(9) . . ?
N3 C11 N2 123.26(10) . . ?
C13 C12 N3 123.04(10) . . ?
C17 C12 N3 116.82(10) . . ?
C17 C12 C13 120.07(10) . . ?
C14 C13 C12 117.64(11) . . ?
C15 C14 C13 123.88(11) . . ?
F2 C14 C13 118.21(11) . . ?
F2 C14 C15 117.91(11) . . ?
C16 C15 C14 117.56(11) . . ?
C17 C16 C15 120.73(11) . . ?
C16 C17 C12 120.08(11) . . ?


_olex2_submission_special_instructions 'No special instructions were received'
loop_
_restr_RIGU_atom_site_label_1
_restr_RIGU_atom_site_label_2
_restr_RIGU_target_weight_param
_restr_RIGU_U13_diff
_restr_RIGU_U23_diff
_restr_RIGU_U33_diff
C4 C5 0.004000 0.006108 -0.002176 0.001021
C4 C6 0.004000 0.008989 -0.003062 0.001370
C4 F3 0.004000 0.002630 0.000304 0.006410
C5 C6 0.004000 0.005531 -0.004096 0.000006
C5 F1 0.004000 0.008991 -0.000152 0.005247
C5 F3 0.004000 0.009182 0.002145 0.008253
C6 F1 0.004000 0.002874 0.001090 0.001320

