# Supplementary Information (SI) for RSC Medicinal Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_sm05db
_database_code_depnum_ccdc_archive 'CCDC 2355435'
loop_
_audit_author_name
_audit_author_address
'Dirk Bockfeld'
;TU Braunschweig
Germany
;
_audit_update_record             
;
2024-05-14 deposited with the CCDC.	2024-07-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H11 N2 O2, C F3 O3 S'

_chemical_formula_sum            'C8 H11 F3 N2 O5 S'
_chemical_formula_weight         304.25

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'
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'
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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.7426(3)
_cell_length_b                   8.8249(3)
_cell_length_c                   15.7395(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1214.34(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    21739
_cell_measurement_theta_min      3.2630
_cell_measurement_theta_max      41.0430

_exptl_crystal_description       irregular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.664
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.408
_exptl_crystal_size_mid          0.287
_exptl_crystal_size_min          0.091
_exptl_absorpt_coefficient_mu    0.325
_shelx_estimated_absorpt_T_min   0.879
_shelx_estimated_absorpt_T_max   0.971
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-7 -10 -1 0.1556
1 11 9 0.1127
-7 6 15 0.1865
-7 -7 15 0.1480
12 1 3 0.1708
-2 -9 15 0.1309
-4 11 -10 0.1342
12 0 1 0.1729
-1 -11 10 0.1403
-2 12 -3 0.1315
-1 12 3 0.1236
0 -12 -3 0.1364
11 -3 -8 0.1881
0 -11 -9 0.1247
-12 -4 2 0.1739
1 6 19 0.0845
-2 -1 -22 0.0286
1 2 22 0.0552
12 4 1 0.1614
0 -2 -22 0.0171
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-6.8385 -10.3379 -0.8225 0.1737 -0.5840 -0.7930
0.7005 11.2409 9.4193 -0.5383 0.7828 0.3123
-6.9405 5.6273 15.3431 -0.7101 0.5456 -0.4451
-6.5469 -6.6058 14.6528 -0.5564 -0.3811 -0.7384
12.1530 0.9830 3.2342 -0.2105 -0.2764 0.9377
-1.5425 -9.2374 14.6142 -0.5509 -0.7169 -0.4273
-3.5570 10.6515 -9.5374 0.3334 0.9412 0.0546
12.3021 0.2187 1.2574 -0.1151 -0.3290 0.9373
-0.7521 -11.2183 9.5167 -0.3068 -0.8646 -0.3978
-2.0818 12.1396 -3.1432 0.0261 0.9835 0.1789
-0.5891 12.2835 3.3749 -0.2732 0.9238 0.2681
-0.2360 -12.3139 -3.1511 0.2673 -0.9043 -0.3327
11.0359 -3.1040 -8.1803 0.3458 -0.5013 0.7932
-0.4976 -11.2323 -9.4940 0.5406 -0.7874 -0.2963
-11.5325 -4.2251 2.0709 0.0039 -0.0081 -1.0000
0.8543 5.8831 19.4858 -0.9336 0.3309 0.1374
-1.6947 -0.8921 -21.9207 0.9953 0.0782 -0.0577
1.2840 2.1210 21.7403 -0.9979 0.0263 0.0600
11.5102 4.3803 1.2993 -0.1558 0.0053 0.9878
0.1526 -1.6062 -22.0007 0.9976 -0.0261 0.0643
_exptl_absorpt_correction_T_min  0.318
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.61a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.777
_oxdiff_exptl_absorpt_empirical_full_max 1.671
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measurement_method       'ω scan'
_diffrn_reflns_number            38656
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.280
_diffrn_reflns_theta_max         41.005
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7712
_reflns_number_gt                7105
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.779
_reflns_Friedel_fraction_max     0.954
_reflns_Friedel_fraction_full    1.000

_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 1.171.40.61a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'

_computing_structure_solution    
'SHELXT 2018/2 (G. M. Sheldrick, Acta Cryst., 2015, A71, 3-8)'
_computing_structure_refinement  
'SHELXL-2018/3 (G. M. Sheldrick, Acta Cryst., 2015, C71, 3-8)'
_computing_molecular_graphics    ?
_computing_publication_material  
'OLEX2 v1.2 (O. V. Dolomanov et al., J. Appl. Cryst., 2009, 42, 339-341)'

_refine_special_details          
;
 All H atoms were placed in idealised positions and refined using a riding
 model, with a common U restrained to be 1.2 (1.5 for methyl groups) times
 the equivalent isotropic displacement parameter of the parent atom.
 Ordered methyl groups were treated as rigid bodies and allowed to
 rotate around the E-CH3 bond.

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0439P)²+0.0515P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2938 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.027(12)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         7712
_refine_ls_number_parameters     175
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0266
_refine_ls_wR_factor_ref         0.0711
_refine_ls_wR_factor_gt          0.0695
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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 0.49659(2) 0.49643(2) 0.43027(2) 0.01415(4) Uani 1 1 d . . . . .
F1 F 0.54366(10) 0.34386(9) 0.57083(4) 0.03030(14) Uani 1 1 d . . . . .
F2 F 0.72480(8) 0.32468(9) 0.47796(7) 0.03587(19) Uani 1 1 d . . . . .
F3 F 0.51327(8) 0.20432(7) 0.45963(5) 0.02562(13) Uani 1 1 d . . . . .
O3 O 0.33709(8) 0.49652(10) 0.45383(5) 0.02393(13) Uani 1 1 d . . . . .
O4 O 0.58361(9) 0.62194(8) 0.46438(5) 0.02078(12) Uani 1 1 d . . . . .
O5 O 0.52762(11) 0.46012(11) 0.34271(5) 0.02786(16) Uani 1 1 d . . . . .
C8 C 0.57387(10) 0.33347(10) 0.48741(6) 0.01802(14) Uani 1 1 d . . . . .
O1 O 0.67631(8) 0.50378(8) 0.16836(4) 0.01783(10) Uani 1 1 d . . . . .
O2 O 0.86445(9) 0.38471(9) 0.24032(5) 0.02355(14) Uani 1 1 d . . . . .
N1 N 0.89171(8) 0.66148(9) 0.34235(5) 0.01513(11) Uani 1 1 d . . . . .
N2 N 0.77662(9) 0.87442(9) 0.31691(5) 0.01671(12) Uani 1 1 d . . . . .
C1 C 0.87321(10) 0.80257(11) 0.36900(6) 0.01735(13) Uani 1 1 d . . . . .
H1 H 0.921002 0.845900 0.417462 0.021 Uiso 1 1 calc R U . . .
C2 C 0.80209(9) 0.64103(9) 0.27062(5) 0.01399(12) Uani 1 1 d . . . . .
C3 C 0.73066(10) 0.77538(9) 0.25483(5) 0.01582(12) Uani 1 1 d . . . . .
H3 H 0.662146 0.796393 0.209491 0.019 Uiso 1 1 calc R U . . .
C4 C 0.99103(13) 0.55141(12) 0.38502(6) 0.02430(17) Uani 1 1 d . . . . .
H4A H 0.930579 0.462916 0.401966 0.036 Uiso 1 1 calc R U . . .
H4B H 1.036533 0.598134 0.435530 0.036 Uiso 1 1 calc R U . . .
H4C H 1.072386 0.519593 0.346074 0.036 Uiso 1 1 calc R U . . .
C5 C 0.73283(13) 1.03419(11) 0.32430(7) 0.02422(18) Uani 1 1 d . . . . .
H5A H 0.742277 1.066487 0.383638 0.036 Uiso 1 1 calc R U . . .
H5B H 0.626701 1.046875 0.305562 0.036 Uiso 1 1 calc R U . . .
H5C H 0.800237 1.096044 0.288628 0.036 Uiso 1 1 calc R U . . .
C6 C 0.78665(9) 0.49539(10) 0.22621(5) 0.01557(11) Uani 1 1 d . . . . .
C7 C 0.64454(13) 0.36449(12) 0.12330(7) 0.02404(17) Uani 1 1 d . . . . .
H7A H 0.731343 0.339379 0.086507 0.036 Uiso 1 1 calc R U . . .
H7B H 0.552376 0.377284 0.088596 0.036 Uiso 1 1 calc R U . . .
H7C H 0.628378 0.282412 0.164269 0.036 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O5 1.4406(8) . ?
S1 O3 1.4429(7) . ?
S1 O4 1.4470(7) . ?
S1 C8 1.8257(9) . ?
F1 C8 1.3424(12) . ?
F2 C8 1.3301(11) . ?
F3 C8 1.3307(11) . ?
O1 C6 1.3287(10) . ?
O1 C7 1.4460(12) . ?
O2 C6 1.2107(11) . ?
N1 C1 1.3238(12) . ?
N1 C2 1.3861(11) . ?
N1 C4 1.4657(12) . ?
N2 C1 1.3369(12) . ?
N2 C3 1.3712(11) . ?
N2 C5 1.4656(12) . ?
C1 H1 0.9500 . ?
C2 C3 1.3628(12) . ?
C2 C6 1.4692(12) . ?
C3 H3 0.9500 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O5 S1 O3 115.34(5) . . ?
O5 S1 O4 115.22(5) . . ?
O3 S1 O4 114.35(5) . . ?
O5 S1 C8 103.08(5) . . ?
O3 S1 C8 103.38(4) . . ?
O4 S1 C8 103.04(4) . . ?
F2 C8 F3 107.96(8) . . ?
F2 C8 F1 107.97(9) . . ?
F3 C8 F1 107.55(8) . . ?
F2 C8 S1 110.98(7) . . ?
F3 C8 S1 111.44(7) . . ?
F1 C8 S1 110.80(6) . . ?
C6 O1 C7 115.35(8) . . ?
C1 N1 C2 108.15(7) . . ?
C1 N1 C4 123.40(8) . . ?
C2 N1 C4 128.45(8) . . ?
C1 N2 C3 108.65(7) . . ?
C1 N2 C5 124.93(8) . . ?
C3 N2 C5 126.38(8) . . ?
N1 C1 N2 109.21(7) . . ?
N1 C1 H1 125.4 . . ?
N2 C1 H1 125.4 . . ?
C3 C2 N1 107.11(7) . . ?
C3 C2 C6 129.21(7) . . ?
N1 C2 C6 123.59(7) . . ?
C2 C3 N2 106.88(7) . . ?
C2 C3 H3 126.6 . . ?
N2 C3 H3 126.6 . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N2 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O2 C6 O1 125.34(8) . . ?
O2 C6 C2 124.53(8) . . ?
O1 C6 C2 110.12(7) . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

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
O5 S1 C8 F2 64.77(8) . . . . ?
O3 S1 C8 F2 -174.78(8) . . . . ?
O4 S1 C8 F2 -55.43(8) . . . . ?
O5 S1 C8 F3 -55.58(7) . . . . ?
O3 S1 C8 F3 64.88(8) . . . . ?
O4 S1 C8 F3 -175.77(6) . . . . ?
O5 S1 C8 F1 -175.29(7) . . . . ?
O3 S1 C8 F1 -54.84(8) . . . . ?
O4 S1 C8 F1 64.51(7) . . . . ?
C2 N1 C1 N2 -0.64(10) . . . . ?
C4 N1 C1 N2 179.79(8) . . . . ?
C3 N2 C1 N1 0.40(10) . . . . ?
C5 N2 C1 N1 -177.62(9) . . . . ?
C1 N1 C2 C3 0.64(9) . . . . ?
C4 N1 C2 C3 -179.83(9) . . . . ?
C1 N1 C2 C6 -176.39(8) . . . . ?
C4 N1 C2 C6 3.14(13) . . . . ?
N1 C2 C3 N2 -0.39(9) . . . . ?
C6 C2 C3 N2 176.42(8) . . . . ?
C1 N2 C3 C2 0.00(10) . . . . ?
C5 N2 C3 C2 177.99(9) . . . . ?
C7 O1 C6 O2 3.61(12) . . . . ?
C7 O1 C6 C2 -176.87(7) . . . . ?
C3 C2 C6 O2 173.56(9) . . . . ?
N1 C2 C6 O2 -10.11(13) . . . . ?
C3 C2 C6 O1 -5.97(12) . . . . ?
N1 C2 C6 O1 170.37(7) . . . . ?

_refine_diff_density_max         0.440
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_sm28db
_database_code_depnum_ccdc_archive 'CCDC 2355439'
loop_
_audit_author_name
_audit_author_address
'Dirk Bockfeld'
;TU Braunschweig
Germany
;
_audit_update_record             
;
2024-05-14 deposited with the CCDC.	2024-07-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H20 Au N4 O4, C F3 O3 S'
_chemical_formula_sum            'C15 H20 Au F3 N4 O7 S'
_chemical_formula_weight         654.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
S S 0.1246 0.1234 '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                   20.6354(11)
_cell_length_b                   6.9529(3)
_cell_length_c                   31.3133(17)
_cell_angle_alpha                90
_cell_angle_beta                 108.983(6)
_cell_angle_gamma                90
_cell_volume                     4248.4(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    20873
_cell_measurement_theta_min      2.8500
_cell_measurement_theta_max      34.3180

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.046
_exptl_crystal_F_000             2528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    7.095
_shelx_estimated_absorpt_T_min   0.260
_shelx_estimated_absorpt_T_max   0.815
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 0 1 0.0622
-2 1 1 0.0912
1 2 0 0.0907
1 1 0 0.0941
24 5 -9 0.1368
1 -1 -1 0.1002
0 0 1 0.0267
0 0 -1 0.0038
13 -9 -4 0.0881
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.9992 0.0000 0.9996 0.0384 -0.0041 0.0569
-1.9992 1.0000 1.0000 0.1230 0.0028 0.0003
0.9996 1.9999 0.0012 0.1504 0.0040 -0.1425
0.9996 1.0000 0.0008 0.0657 -0.0029 -0.0859
24.3537 5.3080 -8.5845 -0.0160 0.0016 -0.9999
0.9996 -1.0000 -1.0003 -0.1041 0.0071 0.0291
-0.0000 0.0001 1.0002 0.0006 -0.0239 -0.0020
0.0000 -0.0001 -1.0002 -0.0006 0.0239 0.0020
12.5611 -8.8324 -4.4951 -0.9873 -0.0778 0.1383
_exptl_absorpt_correction_T_min  0.267
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.64a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.855
_oxdiff_exptl_absorpt_empirical_full_max 1.361
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            147355
_diffrn_reflns_av_unetI/netI     0.0465
_diffrn_reflns_av_R_equivalents  0.0798
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_limit_l_max       48
_diffrn_reflns_theta_min         1.974
_diffrn_reflns_theta_max         33.138
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             16356
_reflns_number_gt                12282
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;


_computing_data_collection       'CrysAlisPro 1.171.42.64a (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.64a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.64a (Rigaku OD, 2022)'

_computing_structure_solution    
'SHELXS-2013/1 (G. M. Sheldrick, Acta Cryst., 2008, A64, 112-122)'
_computing_structure_refinement  
'SHELXL-2018/3 (G. M. Sheldrick, Acta Cryst., 2015, C71, 3-8)'
_computing_molecular_graphics    ?
_computing_publication_material  
'OLEX2 v1.3 (O. V. Dolomanov et al., J. Appl. Cryst., 2009, 42, 339-341)'

_refine_special_details          
;
All H atoms were placed in idealised positions and refined using a riding
model, with a common U restrained to be 1.2 (1.5 for methyl groups) times
the equivalent isotropic displacement parameter of the parent atom.
Ordered methyl groups were treated as rigid bodies and allowed to
rotate around the E-CH3 bond.

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

Refined as a pseudo merohedral 2-component twin. (TWIN 1 0 0 0 -1 0 -1 0 -1 2;
BASF 0.3376)
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+82.4557P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     patterson
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         16356
_refine_ls_number_parameters     572
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0848
_refine_ls_R_factor_gt           0.0618
_refine_ls_wR_factor_ref         0.1211
_refine_ls_wR_factor_gt          0.1143
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.24444(2) 0.52444(4) 0.25249(2) 0.01999(7) Uani 1 1 d . . . . .
O1 O 0.3601(4) 0.3175(13) 0.4458(3) 0.0317(17) Uani 1 1 d . . . . .
O2 O 0.2586(3) 0.3173(12) 0.4585(2) 0.0263(15) Uani 1 1 d . . . . .
O3 O 0.1390(4) 0.6918(13) 0.0554(3) 0.0361(19) Uani 1 1 d . . . . .
O4 O 0.2438(4) 0.6981(11) 0.0473(2) 0.0270(15) Uani 1 1 d . . . . .
N1 N 0.2852(4) 0.4368(11) 0.3526(2) 0.0174(13) Uani 1 1 d . . . . .
N2 N 0.1764(4) 0.4796(12) 0.3252(2) 0.0206(14) Uani 1 1 d . . . . .
N3 N 0.2081(4) 0.5980(11) 0.1514(3) 0.0227(16) Uani 1 1 d . . . . .
N4 N 0.3169(4) 0.5705(11) 0.1830(2) 0.0187(14) Uani 1 1 d . . . . .
C1 C 0.2346(5) 0.4800(14) 0.3137(3) 0.0210(16) Uani 1 1 d . . . . .
C2 C 0.2578(5) 0.4089(14) 0.3875(3) 0.0220(18) Uani 1 1 d . . . . .
C3 C 0.1891(4) 0.4360(13) 0.3695(3) 0.0199(17) Uani 1 1 d . . . . .
H3 H 0.156358 0.426374 0.384880 0.024 Uiso 1 1 calc R U . . .
C4 C 0.3579(5) 0.4267(15) 0.3560(3) 0.0235(18) Uani 1 1 d . . . . .
H4A H 0.383464 0.527913 0.376298 0.035 Uiso 1 1 calc R U . . .
H4B H 0.362159 0.444835 0.325956 0.035 Uiso 1 1 calc R U . . .
H4C H 0.376464 0.300723 0.367862 0.035 Uiso 1 1 calc R U . . .
C5 C 0.1084(5) 0.5311(16) 0.2935(3) 0.027(2) Uani 1 1 d . . . . .
H5A H 0.072701 0.467026 0.302598 0.040 Uiso 1 1 calc R U . . .
H5B H 0.105213 0.489808 0.262921 0.040 Uiso 1 1 calc R U . . .
H5C H 0.102137 0.670774 0.293784 0.040 Uiso 1 1 calc R U . . .
C6 C 0.2993(5) 0.3461(14) 0.4334(3) 0.0236(19) Uani 1 1 d . . . . .
C7 C 0.2909(7) 0.2390(18) 0.5034(4) 0.035(3) Uani 1 1 d . . . . .
H7A H 0.310973 0.113377 0.501076 0.053 Uiso 1 1 calc R U . . .
H7B H 0.256483 0.224120 0.518623 0.053 Uiso 1 1 calc R U . . .
H7C H 0.326953 0.326712 0.520900 0.053 Uiso 1 1 calc R U . . .
C8 C 0.2565(5) 0.5671(13) 0.1918(3) 0.0214(17) Uani 1 1 d . . . . .
C9 C 0.2378(5) 0.6217(13) 0.1178(3) 0.0189(17) Uani 1 1 d . . . . .
C10 C 0.3067(5) 0.6053(13) 0.1383(3) 0.0197(17) Uani 1 1 d . . . . .
H10 H 0.341080 0.615909 0.124236 0.024 Uiso 1 1 calc R U . . .
C11 C 0.1343(5) 0.6078(14) 0.1457(3) 0.0247(19) Uani 1 1 d . . . . .
H11A H 0.116168 0.733178 0.133071 0.037 Uiso 1 1 calc R U . . .
H11B H 0.127735 0.591216 0.175128 0.037 Uiso 1 1 calc R U . . .
H11C H 0.110020 0.505566 0.125196 0.037 Uiso 1 1 calc R U . . .
C12 C 0.3838(5) 0.5384(16) 0.2169(3) 0.0252(19) Uani 1 1 d . . . . .
H12A H 0.381191 0.567338 0.246966 0.038 Uiso 1 1 calc R U . . .
H12B H 0.417799 0.622516 0.210752 0.038 Uiso 1 1 calc R U . . .
H12C H 0.397309 0.403816 0.215885 0.038 Uiso 1 1 calc R U . . .
C13 C 0.2002(6) 0.6725(14) 0.0703(3) 0.025(2) Uani 1 1 d . . . . .
C14 C 0.2141(8) 0.7591(19) 0.0009(4) 0.038(3) Uani 1 1 d . . . . .
H14A H 0.192298 0.885005 -0.000004 0.057 Uiso 1 1 calc R U . . .
H14B H 0.179620 0.665115 -0.015592 0.057 Uiso 1 1 calc R U . . .
H14C H 0.250072 0.768488 -0.013045 0.057 Uiso 1 1 calc R U . . .
Au1A Au 0.25724(2) 0.02816(4) 0.25050(2) 0.01971(7) Uani 1 1 d . . . . .
O1A O 0.1671(4) 0.1893(13) 0.0535(3) 0.0362(19) Uani 1 1 d . . . . .
O2A O 0.0548(4) 0.1777(12) 0.0447(2) 0.0307(17) Uani 1 1 d . . . . .
O3A O 0.3349(4) -0.1772(12) 0.4445(3) 0.0318(17) Uani 1 1 d . . . . .
O4A O 0.4482(4) -0.1653(12) 0.4564(2) 0.0278(15) Uani 1 1 d . . . . .
N1A N 0.1936(4) 0.0994(10) 0.1493(2) 0.0169(14) Uani 1 1 d . . . . .
N2A N 0.1158(4) 0.0740(12) 0.1818(2) 0.0211(15) Uani 1 1 d . . . . .
N3A N 0.3157(4) -0.0601(11) 0.3506(2) 0.0191(14) Uani 1 1 d . . . . .
N4A N 0.3971(4) -0.0236(12) 0.3219(2) 0.0204(14) Uani 1 1 d . . . . .
C1A C 0.1847(4) 0.0689(13) 0.1895(3) 0.0201(17) Uani 1 1 d . . . . .
C2A C 0.1295(5) 0.1208(14) 0.1159(3) 0.0203(17) Uani 1 1 d . . . . .
C3A C 0.0821(5) 0.1042(13) 0.1372(3) 0.0191(17) Uani 1 1 d . . . . .
H3A H 0.033856 0.112253 0.123334 0.023 Uiso 1 1 calc R U . . .
C4A C 0.2614(5) 0.1085(14) 0.1425(4) 0.0244(19) Uani 1 1 d . . . . .
H4AA H 0.297412 0.075392 0.170762 0.037 Uiso 1 1 calc R U . . .
H4AB H 0.269186 0.238886 0.133332 0.037 Uiso 1 1 calc R U . . .
H4AC H 0.262401 0.017090 0.118890 0.037 Uiso 1 1 calc R U . . .
C5A C 0.0846(5) 0.0449(16) 0.2172(3) 0.027(2) Uani 1 1 d . . . . .
H5AA H 0.047571 0.138355 0.213379 0.041 Uiso 1 1 calc R U . . .
H5AB H 0.119347 0.062468 0.246860 0.041 Uiso 1 1 calc R U . . .
H5AC H 0.065886 -0.085745 0.214930 0.041 Uiso 1 1 calc R U . . .
C6A C 0.1213(5) 0.1647(14) 0.0683(3) 0.024(2) Uani 1 1 d . . . . .
C7A C 0.0413(7) 0.235(2) -0.0020(4) 0.039(3) Uani 1 1 d . . . . .
H7AA H 0.061689 0.361671 -0.002976 0.059 Uiso 1 1 calc R U . . .
H7AB H -0.008319 0.241808 -0.017357 0.059 Uiso 1 1 calc R U . . .
H7AC H 0.061377 0.140602 -0.017270 0.059 Uiso 1 1 calc R U . . .
C8A C 0.3276(4) -0.0183(14) 0.3116(3) 0.0218(17) Uani 1 1 d . . . . .
C9A C 0.3777(4) -0.0892(12) 0.3853(3) 0.0176(16) Uani 1 1 d . . . . .
C10A C 0.4276(5) -0.0652(13) 0.3664(3) 0.0190(16) Uani 1 1 d . . . . .
H10A H 0.475468 -0.075643 0.381586 0.023 Uiso 1 1 calc R U . . .
C11A C 0.2463(4) -0.0689(15) 0.3543(3) 0.0236(18) Uani 1 1 d . . . . .
H11D H 0.212090 -0.058195 0.324203 0.035 Uiso 1 1 calc R U . . .
H11E H 0.240309 0.037362 0.373293 0.035 Uiso 1 1 calc R U . . .
H11F H 0.240334 -0.191569 0.368009 0.035 Uiso 1 1 calc R U . . .
C12A C 0.4336(5) 0.0247(15) 0.2902(3) 0.0252(19) Uani 1 1 d . . . . .
H12D H 0.450161 0.157609 0.295272 0.038 Uiso 1 1 calc R U . . .
H12E H 0.402405 0.011317 0.259128 0.038 Uiso 1 1 calc R U . . .
H12F H 0.472619 -0.062518 0.294884 0.038 Uiso 1 1 calc R U . . .
C13A C 0.3823(5) -0.1471(14) 0.4315(3) 0.0219(18) Uani 1 1 d . . . . .
C14A C 0.4584(7) -0.2351(19) 0.5019(3) 0.035(3) Uani 1 1 d . . . . .
H14D H 0.507638 -0.242348 0.518504 0.053 Uiso 1 1 calc R U . . .
H14E H 0.438050 -0.363281 0.500355 0.053 Uiso 1 1 calc R U . . .
H14F H 0.436550 -0.146862 0.517408 0.053 Uiso 1 1 calc R U . . .
S1 S 0.54764(12) 0.5684(4) 0.34086(7) 0.0217(4) Uani 1 1 d . . . . .
F1 F 0.6247(3) 0.4256(10) 0.41840(19) 0.0356(14) Uani 1 1 d . . . . .
F2 F 0.5323(4) 0.2662(10) 0.3868(2) 0.049(2) Uani 1 1 d . . . . .
F3 F 0.5282(4) 0.5391(12) 0.4193(2) 0.0435(17) Uani 1 1 d . . . . .
O5 O 0.4746(3) 0.5679(12) 0.3197(2) 0.0302(16) Uani 1 1 d . . . . .
O6 O 0.5766(4) 0.7557(11) 0.3556(3) 0.0380(19) Uani 1 1 d . . . . .
O7 O 0.5858(4) 0.4507(13) 0.3193(2) 0.0334(17) Uani 1 1 d . . . . .
C15 C 0.5593(5) 0.4439(14) 0.3937(3) 0.0253(19) Uani 1 1 d . . . . .
S1A S 0.04102(13) 0.0729(4) 0.33979(7) 0.0253(5) Uani 1 1 d . . . . .
F1A F 0.0347(4) -0.0492(12) 0.4179(2) 0.0458(17) Uani 1 1 d . . . . .
F2A F 0.1330(4) 0.0602(12) 0.4198(2) 0.0480(19) Uani 1 1 d . . . . .
F3A F 0.0993(4) -0.2192(10) 0.3900(3) 0.0500(19) Uani 1 1 d . . . . .
O5A O 0.0954(4) 0.0689(12) 0.3204(2) 0.0323(17) Uani 1 1 d . . . . .
O6A O -0.0169(4) -0.0464(14) 0.3181(2) 0.0372(18) Uani 1 1 d . . . . .
O7A O 0.0246(4) 0.2634(11) 0.3523(3) 0.0366(18) Uani 1 1 d . . . . .
C15A C 0.0788(6) -0.0388(17) 0.3945(3) 0.033(2) 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
Au1 C1 2.014(9) . ?
Au1 C8 2.016(9) . ?
O1 C6 1.204(12) . ?
O2 C6 1.338(12) . ?
O2 C7 1.452(13) . ?
O3 C13 1.204(13) . ?
O4 C13 1.333(13) . ?
O4 C14 1.445(13) . ?
N1 C1 1.357(11) . ?
N1 C2 1.397(11) . ?
N1 C4 1.471(11) . ?
N2 C3 1.361(11) . ?
N2 C1 1.363(11) . ?
N2 C5 1.475(12) . ?
N3 C8 1.350(12) . ?
N3 C9 1.390(12) . ?
N3 C11 1.476(12) . ?
N4 C8 1.362(12) . ?
N4 C10 1.369(11) . ?
N4 C12 1.460(11) . ?
C2 C3 1.359(12) . ?
C2 C6 1.480(13) . ?
C9 C10 1.363(13) . ?
C9 C13 1.478(12) . ?
Au1A C8A 2.017(8) . ?
Au1A C1A 2.028(8) . ?
O1A C6A 1.195(13) . ?
O2A C6A 1.333(11) . ?
O2A C7A 1.455(12) . ?
O3A C13A 1.196(12) . ?
O4A C13A 1.336(11) . ?
O4A C14A 1.452(12) . ?
N1A C1A 1.345(11) . ?
N1A C2A 1.402(11) . ?
N1A C4A 1.484(11) . ?
N2A C3A 1.359(11) . ?
N2A C1A 1.364(12) . ?
N2A C5A 1.466(12) . ?
N3A C8A 1.351(11) . ?
N3A C9A 1.399(11) . ?
N3A C11A 1.477(11) . ?
N4A C10A 1.361(10) . ?
N4A C8A 1.365(11) . ?
N4A C12A 1.469(11) . ?
C2A C3A 1.356(13) . ?
C2A C6A 1.474(13) . ?
C9A C10A 1.353(12) . ?
C9A C13A 1.474(12) . ?
S1 O5 1.435(7) . ?
S1 O6 1.445(8) . ?
S1 O7 1.445(7) . ?
S1 C15 1.813(9) . ?
F1 C15 1.326(11) . ?
F2 C15 1.343(12) . ?
F3 C15 1.352(11) . ?
S1A O6A 1.432(8) . ?
S1A O5A 1.439(7) . ?
S1A O7A 1.452(8) . ?
S1A C15A 1.811(10) . ?
F1A C15A 1.343(13) . ?
F2A C15A 1.331(12) . ?
F3A C15A 1.346(13) . ?

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 C8 178.7(4) . . ?
C6 O2 C7 116.5(9) . . ?
C13 O4 C14 116.2(9) . . ?
C1 N1 C2 110.2(7) . . ?
C1 N1 C4 122.9(7) . . ?
C2 N1 C4 126.9(7) . . ?
C3 N2 C1 112.1(7) . . ?
C3 N2 C5 124.5(7) . . ?
C1 N2 C5 123.3(7) . . ?
C8 N3 C9 110.8(8) . . ?
C8 N3 C11 122.7(8) . . ?
C9 N3 C11 126.4(8) . . ?
C8 N4 C10 111.5(7) . . ?
C8 N4 C12 124.1(7) . . ?
C10 N4 C12 124.4(8) . . ?
N1 C1 N2 104.4(7) . . ?
N1 C1 Au1 127.1(6) . . ?
N2 C1 Au1 128.5(6) . . ?
C3 C2 N1 106.9(8) . . ?
C3 C2 C6 129.7(9) . . ?
N1 C2 C6 123.3(8) . . ?
C2 C3 N2 106.4(8) . . ?
O1 C6 O2 125.0(9) . . ?
O1 C6 C2 125.1(9) . . ?
O2 C6 C2 109.9(9) . . ?
N3 C8 N4 104.7(8) . . ?
N3 C8 Au1 128.7(7) . . ?
N4 C8 Au1 126.6(6) . . ?
C10 C9 N3 106.5(8) . . ?
C10 C9 C13 128.2(9) . . ?
N3 C9 C13 125.1(9) . . ?
C9 C10 N4 106.5(8) . . ?
O3 C13 O4 125.6(9) . . ?
O3 C13 C9 123.9(10) . . ?
O4 C13 C9 110.5(9) . . ?
C8A Au1A C1A 178.3(4) . . ?
C6A O2A C7A 113.7(9) . . ?
C13A O4A C14A 113.6(9) . . ?
C1A N1A C2A 109.5(7) . . ?
C1A N1A C4A 124.2(8) . . ?
C2A N1A C4A 126.3(8) . . ?
C3A N2A C1A 109.9(8) . . ?
C3A N2A C5A 126.5(8) . . ?
C1A N2A C5A 123.6(8) . . ?
C8A N3A C9A 110.2(7) . . ?
C8A N3A C11A 123.1(7) . . ?
C9A N3A C11A 126.7(7) . . ?
C10A N4A C8A 110.3(7) . . ?
C10A N4A C12A 125.1(8) . . ?
C8A N4A C12A 124.5(7) . . ?
N1A C1A N2A 106.4(7) . . ?
N1A C1A Au1A 128.3(7) . . ?
N2A C1A Au1A 125.3(7) . . ?
C3A C2A N1A 106.2(7) . . ?
C3A C2A C6A 130.5(8) . . ?
N1A C2A C6A 123.2(8) . . ?
C2A C3A N2A 108.0(8) . . ?
O1A C6A O2A 125.2(9) . . ?
O1A C6A C2A 125.3(9) . . ?
O2A C6A C2A 109.5(9) . . ?
N3A C8A N4A 105.4(7) . . ?
N3A C8A Au1A 127.3(6) . . ?
N4A C8A Au1A 127.2(6) . . ?
C10A C9A N3A 105.9(7) . . ?
C10A C9A C13A 130.4(8) . . ?
N3A C9A C13A 123.6(8) . . ?
C9A C10A N4A 108.1(8) . . ?
O3A C13A O4A 125.1(9) . . ?
O3A C13A C9A 125.8(8) . . ?
O4A C13A C9A 109.1(8) . . ?
O5 S1 O6 114.4(5) . . ?
O5 S1 O7 115.6(4) . . ?
O6 S1 O7 115.4(5) . . ?
O5 S1 C15 103.1(4) . . ?
O6 S1 C15 102.7(5) . . ?
O7 S1 C15 103.0(5) . . ?
F1 C15 F2 107.2(8) . . ?
F1 C15 F3 106.9(7) . . ?
F2 C15 F3 107.2(9) . . ?
F1 C15 S1 112.6(7) . . ?
F2 C15 S1 111.6(6) . . ?
F3 C15 S1 111.1(7) . . ?
O6A S1A O5A 115.8(5) . . ?
O6A S1A O7A 115.1(5) . . ?
O5A S1A O7A 114.4(5) . . ?
O6A S1A C15A 103.7(5) . . ?
O5A S1A C15A 103.7(5) . . ?
O7A S1A C15A 101.7(5) . . ?
F2A C15A F1A 106.9(8) . . ?
F2A C15A F3A 108.2(10) . . ?
F1A C15A F3A 107.4(9) . . ?
F2A C15A S1A 111.2(8) . . ?
F1A C15A S1A 112.3(8) . . ?
F3A C15A S1A 110.6(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 C1 N2 0.5(10) . . . . ?
C4 N1 C1 N2 -178.4(8) . . . . ?
C2 N1 C1 Au1 -177.6(7) . . . . ?
C4 N1 C1 Au1 3.6(13) . . . . ?
C3 N2 C1 N1 -0.7(11) . . . . ?
C5 N2 C1 N1 176.3(8) . . . . ?
C3 N2 C1 Au1 177.3(7) . . . . ?
C5 N2 C1 Au1 -5.7(14) . . . . ?
C1 N1 C2 C3 -0.1(11) . . . . ?
C4 N1 C2 C3 178.6(9) . . . . ?
C1 N1 C2 C6 175.4(9) . . . . ?
C4 N1 C2 C6 -5.8(15) . . . . ?
N1 C2 C3 N2 -0.3(11) . . . . ?
C6 C2 C3 N2 -175.4(10) . . . . ?
C1 N2 C3 C2 0.6(11) . . . . ?
C5 N2 C3 C2 -176.3(9) . . . . ?
C7 O2 C6 O1 -2.4(15) . . . . ?
C7 O2 C6 C2 174.8(9) . . . . ?
C3 C2 C6 O1 176.5(11) . . . . ?
N1 C2 C6 O1 2.0(16) . . . . ?
C3 C2 C6 O2 -0.8(15) . . . . ?
N1 C2 C6 O2 -175.2(9) . . . . ?
C9 N3 C8 N4 -0.4(10) . . . . ?
C11 N3 C8 N4 -179.3(8) . . . . ?
C9 N3 C8 Au1 179.7(7) . . . . ?
C11 N3 C8 Au1 0.8(13) . . . . ?
C10 N4 C8 N3 0.8(10) . . . . ?
C12 N4 C8 N3 -178.4(8) . . . . ?
C10 N4 C8 Au1 -179.3(7) . . . . ?
C12 N4 C8 Au1 1.5(13) . . . . ?
C8 N3 C9 C10 -0.1(10) . . . . ?
C11 N3 C9 C10 178.7(9) . . . . ?
C8 N3 C9 C13 -175.1(8) . . . . ?
C11 N3 C9 C13 3.7(14) . . . . ?
N3 C9 C10 N4 0.6(10) . . . . ?
C13 C9 C10 N4 175.4(9) . . . . ?
C8 N4 C10 C9 -1.0(11) . . . . ?
C12 N4 C10 C9 178.3(9) . . . . ?
C14 O4 C13 O3 1.8(15) . . . . ?
C14 O4 C13 C9 -176.6(9) . . . . ?
C10 C9 C13 O3 -176.8(10) . . . . ?
N3 C9 C13 O3 -2.9(16) . . . . ?
C10 C9 C13 O4 1.7(14) . . . . ?
N3 C9 C13 O4 175.5(8) . . . . ?
C2A N1A C1A N2A -1.0(10) . . . . ?
C4A N1A C1A N2A 179.0(8) . . . . ?
C2A N1A C1A Au1A -179.8(7) . . . . ?
C4A N1A C1A Au1A 0.2(13) . . . . ?
C3A N2A C1A N1A 1.0(10) . . . . ?
C5A N2A C1A N1A 179.4(8) . . . . ?
C3A N2A C1A Au1A 179.9(6) . . . . ?
C5A N2A C1A Au1A -1.8(13) . . . . ?
C1A N1A C2A C3A 0.6(10) . . . . ?
C4A N1A C2A C3A -179.4(8) . . . . ?
C1A N1A C2A C6A 177.2(9) . . . . ?
C4A N1A C2A C6A -2.8(14) . . . . ?
N1A C2A C3A N2A 0.0(10) . . . . ?
C6A C2A C3A N2A -176.2(10) . . . . ?
C1A N2A C3A C2A -0.7(11) . . . . ?
C5A N2A C3A C2A -178.9(9) . . . . ?
C7A O2A C6A O1A -2.8(16) . . . . ?
C7A O2A C6A C2A 175.6(9) . . . . ?
C3A C2A C6A O1A 174.5(11) . . . . ?
N1A C2A C6A O1A -1.2(16) . . . . ?
C3A C2A C6A O2A -3.9(15) . . . . ?
N1A C2A C6A O2A -179.6(8) . . . . ?
C9A N3A C8A N4A 0.7(10) . . . . ?
C11A N3A C8A N4A 179.8(8) . . . . ?
C9A N3A C8A Au1A 177.8(7) . . . . ?
C11A N3A C8A Au1A -3.1(14) . . . . ?
C10A N4A C8A N3A -0.8(11) . . . . ?
C12A N4A C8A N3A -176.1(8) . . . . ?
C10A N4A C8A Au1A -177.9(7) . . . . ?
C12A N4A C8A Au1A 6.8(14) . . . . ?
C8A N3A C9A C10A -0.4(10) . . . . ?
C11A N3A C9A C10A -179.4(9) . . . . ?
C8A N3A C9A C13A -176.7(9) . . . . ?
C11A N3A C9A C13A 4.3(14) . . . . ?
N3A C9A C10A N4A -0.1(10) . . . . ?
C13A C9A C10A N4A 175.8(9) . . . . ?
C8A N4A C10A C9A 0.6(11) . . . . ?
C12A N4A C10A C9A 175.9(9) . . . . ?
C14A O4A C13A O3A 2.6(15) . . . . ?
C14A O4A C13A C9A -176.0(9) . . . . ?
C10A C9A C13A O3A -174.7(10) . . . . ?
N3A C9A C13A O3A 0.7(16) . . . . ?
C10A C9A C13A O4A 3.9(14) . . . . ?
N3A C9A C13A O4A 179.2(8) . . . . ?
O5 S1 C15 F1 178.8(7) . . . . ?
O6 S1 C15 F1 -62.1(8) . . . . ?
O7 S1 C15 F1 58.1(8) . . . . ?
O5 S1 C15 F2 58.2(8) . . . . ?
O6 S1 C15 F2 177.4(8) . . . . ?
O7 S1 C15 F2 -62.4(8) . . . . ?
O5 S1 C15 F3 -61.4(8) . . . . ?
O6 S1 C15 F3 57.8(8) . . . . ?
O7 S1 C15 F3 178.0(7) . . . . ?
O6A S1A C15A F2A -178.0(8) . . . . ?
O5A S1A C15A F2A 60.7(9) . . . . ?
O7A S1A C15A F2A -58.2(9) . . . . ?
O6A S1A C15A F1A -58.3(9) . . . . ?
O5A S1A C15A F1A -179.6(8) . . . . ?
O7A S1A C15A F1A 61.5(9) . . . . ?
O6A S1A C15A F3A 61.7(9) . . . . ?
O5A S1A C15A F3A -59.6(9) . . . . ?
O7A S1A C15A F3A -178.6(8) . . . . ?

_refine_diff_density_max         4.018
_refine_diff_density_min         -5.653
_refine_diff_density_rms         0.225

####################################################################### 
# 
# 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_sm23db
_database_code_depnum_ccdc_archive 'CCDC 2355436'
loop_
_audit_author_name
_audit_author_address
'Dirk Bockfeld'
;TU Braunschweig
Germany
;
_audit_update_record             
;
2024-05-14 deposited with the CCDC.	2024-07-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H13 N2 O2, B F4'
_chemical_formula_sum            'C8 H13 B F4 N2 O2'
_chemical_formula_weight         256.01

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   8.1082(7)
_cell_length_b                   8.1979(10)
_cell_length_c                   9.6164(11)
_cell_angle_alpha                79.200(10)
_cell_angle_beta                 88.373(8)
_cell_angle_gamma                66.083(10)
_cell_volume                     573.16(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4175
_cell_measurement_theta_min      4.6820
_cell_measurement_theta_max      72.5750

_exptl_crystal_description       irregular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_F_000             264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    1.296
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 -4 0 0.0324
4 4 -2 0.0212
-3 3 0 0.0290
-4 -4 2 0.0205
-1 -1 -6 0.0057
1 1 6 0.0019
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.8447 -3.7151 0.0562 0.2135 0.6023 0.7692
4.1373 4.0361 -1.6584 -0.2993 -0.8471 0.4391
-2.5300 3.1854 0.1984 -0.1726 -0.4867 -0.8563
-3.8818 -4.2581 1.6239 0.3105 0.8785 -0.3630
-0.8857 -0.9355 -6.1636 -0.9915 0.1301 0.0093
0.8857 0.9355 6.1636 0.9915 -0.1301 -0.0093
_exptl_absorpt_correction_T_min  0.49233
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.64a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.636
_oxdiff_exptl_absorpt_empirical_full_max 1.691
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            6548
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.688
_diffrn_reflns_theta_max         66.596
_diffrn_reflns_theta_full        66.596
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6548
_reflns_number_gt                4438
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'CrysAlisPro 1.171.42.64a (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.64a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.64a (Rigaku OD, 2022)'

_computing_structure_solution    
'SHELXT 2018/2 (G. M. Sheldrick, Acta Cryst., 2015, A71, 3-8)'
_computing_structure_refinement  
'SHELXL-2018/3 (G. M. Sheldrick, Acta Cryst., 2015, C71, 3-8)'
_computing_molecular_graphics    ?
_computing_publication_material  
'OLEX2 v1.3 (O. V. Dolomanov et al., J. Appl. Cryst., 2009, 42, 339-341)'

_refine_special_details          
;
 All H atoms were placed in idealised positions and refined using a riding
 model, with a common U restrained to be 1.2 (1.5 for methyl groups) times
 the equivalent isotropic displacement parameter of the parent atom.
 Ordered methyl groups were treated as rigid bodies and allowed to
 rotate around the E-CH3 bond.

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

 Refined as a 2-component twin. Component 2 rotated by 179.8790°
 around [0.71 0.71 -0.01] (reciprocal) or [0.69 0.71 -0.14] (direct)
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6548
_refine_ls_number_parameters     158
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1366
_refine_ls_R_factor_gt           0.1020
_refine_ls_wR_factor_ref         0.2979
_refine_ls_wR_factor_gt          0.2657
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_restrained_S_all      1.102
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
F1 F 0.2828(5) 0.5427(5) 0.9246(3) 0.0534(9) Uani 1 1 d . . . . .
F2 F 0.2728(4) 0.5474(4) 0.6893(3) 0.0508(9) Uani 1 1 d . . . . .
F3 F 0.4468(5) 0.2885(5) 0.8361(5) 0.0735(12) Uani 1 1 d . . . . .
F4 F 0.1414(6) 0.3931(6) 0.8360(4) 0.0692(11) Uani 1 1 d . . . . .
B1 B 0.2850(9) 0.4411(8) 0.8215(6) 0.0432(14) Uani 1 1 d . . . . .
O1 O 0.1404(5) 1.1065(5) 0.5632(4) 0.0484(10) Uani 1 1 d . . . . .
O2 O 0.2677(5) 0.9975(5) 0.3694(4) 0.0424(9) Uani 1 1 d . . . . .
N1 N 0.4446(6) 0.8035(6) 0.7315(5) 0.0388(10) Uani 1 1 d . . . . .
N2 N 0.6503(6) 0.5822(6) 0.6498(5) 0.0409(10) Uani 1 1 d . . . . .
C1 C 0.5855(7) 0.6473(7) 0.7665(6) 0.0420(12) Uani 1 1 d . . . . .
H1 H 0.633679 0.589689 0.860417 0.050 Uiso 1 1 calc R U . . .
C2 C 0.4128(7) 0.8401(7) 0.5862(5) 0.0374(11) Uani 1 1 d . . . . .
C3 C 0.5429(7) 0.7010(7) 0.5354(5) 0.0387(11) Uani 1 1 d . . . . .
H3 H 0.556699 0.688569 0.438987 0.046 Uiso 1 1 calc R U . . .
C4 C 0.3424(8) 0.9132(8) 0.8349(6) 0.0459(13) Uani 1 1 d . . . . .
H4A H 0.216846 0.926443 0.830818 0.069 Uiso 1 1 calc R U . . .
H4B H 0.345318 1.033589 0.812234 0.069 Uiso 1 1 calc R U . . .
H4C H 0.396927 0.852532 0.930418 0.069 Uiso 1 1 calc R U . . .
C5 C 0.8031(7) 0.4087(7) 0.6472(6) 0.0486(14) Uani 1 1 d . . . . .
H5A H 0.762615 0.309624 0.669856 0.073 Uiso 1 1 calc R U . . .
H5B H 0.897570 0.389684 0.717462 0.073 Uiso 1 1 calc R U . . .
H5C H 0.851424 0.410566 0.552656 0.073 Uiso 1 1 calc R U . . .
C6 C 0.2593(7) 0.9970(7) 0.5079(6) 0.0404(12) Uani 1 1 d . . . . .
C7 C 0.1143(8) 1.1375(8) 0.2794(6) 0.0444(12) Uani 1 1 d . . . . .
H7A H 0.105738 1.260086 0.284794 0.053 Uiso 1 1 calc R U . . .
H7B H 0.000211 1.128890 0.310616 0.053 Uiso 1 1 calc R U . . .
C8 C 0.1466(8) 1.1048(9) 0.1313(6) 0.0524(14) Uani 1 1 d . . . . .
H8A H 0.146017 0.986842 0.126061 0.079 Uiso 1 1 calc R U . . .
H8B H 0.263986 1.105007 0.104290 0.079 Uiso 1 1 calc R U . . .
H8C H 0.050963 1.201259 0.066511 0.079 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 B1 1.404(7) . ?
F2 B1 1.381(7) . ?
F3 B1 1.385(7) . ?
F4 B1 1.368(8) . ?
O1 C6 1.212(6) . ?
O2 C6 1.331(7) . ?
O2 C7 1.464(6) . ?
N1 C1 1.316(7) . ?
N1 C2 1.382(7) . ?
N1 C4 1.472(7) . ?
N2 C1 1.336(7) . ?
N2 C3 1.372(7) . ?
N2 C5 1.463(7) . ?
C2 C3 1.362(7) . ?
C2 C6 1.470(7) . ?
C7 C8 1.494(8) . ?

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
F4 B1 F2 109.8(5) . . ?
F4 B1 F3 110.9(5) . . ?
F2 B1 F3 108.6(5) . . ?
F4 B1 F1 109.6(5) . . ?
F2 B1 F1 108.4(5) . . ?
F3 B1 F1 109.5(5) . . ?
C6 O2 C7 116.2(4) . . ?
C1 N1 C2 108.2(4) . . ?
C1 N1 C4 123.7(4) . . ?
C2 N1 C4 128.1(4) . . ?
C1 N2 C3 108.1(4) . . ?
C1 N2 C5 125.3(5) . . ?
C3 N2 C5 126.5(4) . . ?
N1 C1 N2 109.7(5) . . ?
C3 C2 N1 107.0(4) . . ?
C3 C2 C6 128.5(5) . . ?
N1 C2 C6 124.4(4) . . ?
C2 C3 N2 107.0(4) . . ?
O1 C6 O2 125.4(5) . . ?
O1 C6 C2 124.2(5) . . ?
O2 C6 C2 110.4(4) . . ?
O2 C7 C8 106.9(4) . . ?

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
C2 N1 C1 N2 1.6(6) . . . . ?
C4 N1 C1 N2 -179.2(5) . . . . ?
C3 N2 C1 N1 -1.3(6) . . . . ?
C5 N2 C1 N1 -178.1(5) . . . . ?
C1 N1 C2 C3 -1.2(5) . . . . ?
C4 N1 C2 C3 179.6(5) . . . . ?
C1 N1 C2 C6 175.8(5) . . . . ?
C4 N1 C2 C6 -3.4(8) . . . . ?
N1 C2 C3 N2 0.4(5) . . . . ?
C6 C2 C3 N2 -176.5(5) . . . . ?
C1 N2 C3 C2 0.5(6) . . . . ?
C5 N2 C3 C2 177.3(5) . . . . ?
C7 O2 C6 O1 -3.5(7) . . . . ?
C7 O2 C6 C2 174.8(4) . . . . ?
C3 C2 C6 O1 173.2(5) . . . . ?
N1 C2 C6 O1 -3.2(8) . . . . ?
C3 C2 C6 O2 -5.1(7) . . . . ?
N1 C2 C6 O2 178.6(4) . . . . ?
C6 O2 C7 C8 -176.3(4) . . . . ?

_refine_diff_density_max         0.579
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.108

####################################################################### 
# 
# 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_sm30db
_database_code_depnum_ccdc_archive 'CCDC 2355443'
loop_
_audit_author_name
_audit_author_address
'Dirk Bockfeld'
;TU Braunschweig
Germany
;
_audit_update_record             
;
2024-05-14 deposited with the CCDC.	2024-07-30 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT971_sm30db              
;
PROBLEM: Check Calcd Resid. Dens.
RESPONSE: The residual density can be attributed to absorption effects.
 Additionally, the dataset was recorded to a very high diffraction angle.
 Usually larger residual electron density is observed in these cases.
;
_vrf_PLAT972_sm30db              
;
PROBLEM: Check Calcd Resid. Dens.
RESPONSE: The residual density can be attributed to absorption effects.
 Additionally, the dataset was recorded to a very high diffraction angle.
 Usually larger residual electron density is observed in these cases.
;
_vrf_PLAT973_sm30db              
;
PROBLEM: Check Calcd Resid. Dens.
RESPONSE: The residual density can be attributed to absorption effects.
 Additionally, the dataset was recorded to a very high diffraction angle.
 Usually larger residual electron density is observed in these cases.
;
# end Validation Reply Form


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H12 Au Cl3 N2 O2, C D Cl3'
_chemical_formula_sum            'C9 H12 Au Cl6 D N2 O2'
_chemical_formula_weight         591.89

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
D D 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'
O O 0.0106 0.0060 '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                   8.2100(2)
_cell_length_b                   11.0977(2)
_cell_length_c                   19.0738(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.627(2)
_cell_angle_gamma                90
_cell_volume                     1718.19(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    57730
_cell_measurement_theta_min      2.1640
_cell_measurement_theta_max      67.7230

_exptl_crystal_description       irregular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.288
_exptl_crystal_F_000             1112
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.630
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    9.495
_shelx_estimated_absorpt_T_min   0.066
_shelx_estimated_absorpt_T_max   0.421
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-10 4 -5 0.1710
1 -12 15 0.1065
-3 12 -15 0.1101
-11 2 3 0.2182
0 9 22 0.0488
0 -9 -22 0.0558
-7 -6 -16 0.1411
3 12 -16 0.1141
9 9 -11 0.2586
-3 -12 16 0.1511
8 5 15 0.2846
1 -14 -11 0.0656
-1 14 11 0.0789
-7 12 9 0.1331
-4 -13 -10 0.1259
0 0 1 0.0654
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-10.4601 4.2686 -5.1316 0.0657 0.2782 0.9583
1.1996 -12.4276 15.4848 -0.2264 -0.9438 -0.2408
-2.7474 11.9877 -14.9070 0.2165 0.9031 0.3708
-11.4544 2.1559 2.9175 0.1566 -0.0388 0.9869
-0.4578 9.1209 21.7426 0.9697 -0.2328 -0.0741
0.3505 -9.1077 -21.7322 -0.9690 0.2326 0.0835
-7.0427 -6.0909 -15.9585 -0.6946 0.1660 0.7000
3.1931 12.4053 -15.5498 0.2310 0.9625 -0.1422
8.8565 8.8521 -11.2630 0.1716 0.7182 -0.6744
-2.9690 -12.4533 15.6039 -0.2316 -0.9651 0.1222
7.9998 5.0004 15.0027 0.6200 -0.1805 -0.7805
1.0002 -14.0002 -11.0014 -0.9454 -0.2680 -0.0567
-1.0002 14.0002 11.0014 0.9454 0.2680 0.0567
-7.0001 11.9999 8.9997 0.7898 0.2169 0.5874
-3.9997 -13.0003 -10.0024 -0.8809 -0.2748 0.3760
-0.0000 0.0000 1.0000 0.0243 -0.0280 -0.0065
_exptl_absorpt_correction_T_min  0.126
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.64a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.841
_oxdiff_exptl_absorpt_empirical_full_max 1.270
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            293238
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_av_R_equivalents  0.0897
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_theta_min         2.129
_diffrn_reflns_theta_max         62.673
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             28103
_reflns_number_gt                20496
_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 1.171.42.64a (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.64a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.64a (Rigaku OD, 2022)'

_computing_structure_solution    
'SHELXT 2018/2 (G. M. Sheldrick, Acta Cryst., 2015, A71, 3-8)'
_computing_structure_refinement  
'SHELXL-2018/3 (G. M. Sheldrick, Acta Cryst., 2015, C71, 3-8)'
_computing_molecular_graphics    ?
_computing_publication_material  
'OLEX2 v1.3 (O. V. Dolomanov et al., J. Appl. Cryst., 2009, 42, 339-341)'

_refine_special_details          
;
 All H atoms were placed in idealised positions and refined using a riding
 model, with a common U restrained to be 1.2 (1.5 for methyl groups) times
 the equivalent isotropic displacement parameter of the parent atom.
 Ordered methyl groups were treated as rigid bodies and allowed to
 rotate around the E-CH3 bond.

 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0170P)²+1.7815P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.00055(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         28103
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0344
_refine_ls_wR_factor_ref         0.0676
_refine_ls_wR_factor_gt          0.0614
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.010
_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 0.41278(2) 0.56016(2) 0.59901(2) 0.01080(1) Uani 1 1 d . . . . .
Cl1 Cl 0.65778(4) 0.58924(3) 0.55489(2) 0.01613(5) Uani 1 1 d . . . . .
Cl2 Cl 0.30709(5) 0.73455(3) 0.54748(2) 0.01837(5) Uani 1 1 d . . . . .
Cl3 Cl 0.50930(4) 0.38636(3) 0.65419(2) 0.01846(5) Uani 1 1 d . . . . .
O1 O -0.20270(15) 0.55266(11) 0.77398(7) 0.01923(18) Uani 1 1 d . . . . .
O2 O -0.02132(17) 0.70455(11) 0.80338(7) 0.02010(18) Uani 1 1 d . . . . .
N1 N 0.08596(14) 0.45891(10) 0.62455(6) 0.01331(14) Uani 1 1 d . . . . .
N2 N 0.16713(14) 0.60613(9) 0.69639(6) 0.01267(13) Uani 1 1 d . . . . .
C1 C 0.20717(15) 0.54058(11) 0.64235(7) 0.01262(15) Uani 1 1 d . . . . .
C2 C -0.03193(16) 0.47227(11) 0.66788(7) 0.01387(16) Uani 1 1 d . . . . .
H2 H -0.129809 0.426088 0.666439 0.017 Uiso 1 1 calc R U . . .
C3 C 0.01783(15) 0.56421(11) 0.71334(7) 0.01350(15) Uani 1 1 d . . . . .
C4 C 0.07762(19) 0.37019(13) 0.56719(8) 0.01703(19) Uani 1 1 d . . . . .
H4A H 0.187671 0.336969 0.565762 0.026 Uiso 1 1 calc R U . . .
H4B H 0.037215 0.409267 0.521835 0.026 Uiso 1 1 calc R U . . .
H4C H 0.002385 0.305006 0.575622 0.026 Uiso 1 1 calc R U . . .
C5 C 0.26512(18) 0.70505(13) 0.73187(8) 0.01703(19) Uani 1 1 d . . . . .
H5A H 0.202570 0.780368 0.724521 0.026 Uiso 1 1 calc R U . . .
H5B H 0.368046 0.712830 0.712045 0.026 Uiso 1 1 calc R U . . .
H5C H 0.290276 0.688112 0.782769 0.026 Uiso 1 1 calc R U . . .
C6 C -0.06724(16) 0.61639(11) 0.76878(7) 0.01447(17) Uani 1 1 d . . . . .
C7 C -0.3092(2) 0.60086(15) 0.82166(10) 0.0212(2) Uani 1 1 d . . . . .
H7A H -0.423542 0.573240 0.806038 0.025 Uiso 1 1 calc R U . . .
H7B H -0.308400 0.689963 0.819270 0.025 Uiso 1 1 calc R U . . .
C8 C -0.2546(3) 0.56142(17) 0.89749(11) 0.0257(3) Uani 1 1 d . . . . .
H8A H -0.325163 0.599193 0.928352 0.038 Uiso 1 1 calc R U . . .
H8B H -0.140003 0.585960 0.912534 0.038 Uiso 1 1 calc R U . . .
H8C H -0.263206 0.473579 0.900685 0.038 Uiso 1 1 calc R U . . .
Cl4 Cl 0.29866(7) -0.03890(4) 0.42172(3) 0.02708(8) Uani 1 1 d . . . . .
Cl5 Cl 0.07319(5) 0.16284(5) 0.40054(3) 0.02896(9) Uani 1 1 d . . . . .
Cl6 Cl 0.32755(6) 0.13368(4) 0.31035(2) 0.02606(7) Uani 1 1 d . . . . .
C9 C 0.2757(2) 0.11390(14) 0.39641(9) 0.0193(2) Uani 1 1 d . . . . .
D9 D 0.353172 0.163104 0.430418 0.023 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Au1 C1 1.9997(12) . ?
Au1 Cl3 2.2817(3) . ?
Au1 Cl2 2.2822(3) . ?
Au1 Cl1 2.3165(3) . ?
O1 C6 1.3341(17) . ?
O1 C7 1.4546(19) . ?
O2 C6 1.2084(18) . ?
N1 C1 1.3512(16) . ?
N1 C2 1.3718(17) . ?
N1 C4 1.4659(17) . ?
N2 C1 1.3422(16) . ?
N2 C3 1.3937(16) . ?
N2 C5 1.4652(17) . ?
C2 C3 1.3614(18) . ?
C3 C6 1.4707(18) . ?
C7 C8 1.513(3) . ?
Cl4 C9 1.7655(17) . ?
Cl5 C9 1.7618(17) . ?
Cl6 C9 1.7702(17) . ?

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 Cl3 88.50(4) . . ?
C1 Au1 Cl2 88.86(4) . . ?
Cl3 Au1 Cl2 177.234(14) . . ?
C1 Au1 Cl1 176.53(4) . . ?
Cl3 Au1 Cl1 91.428(13) . . ?
Cl2 Au1 Cl1 91.157(13) . . ?
C6 O1 C7 115.94(12) . . ?
C1 N1 C2 109.62(11) . . ?
C1 N1 C4 126.04(11) . . ?
C2 N1 C4 124.34(11) . . ?
C1 N2 C3 108.81(10) . . ?
C1 N2 C5 125.45(11) . . ?
C3 N2 C5 125.74(11) . . ?
N2 C1 N1 107.49(11) . . ?
N2 C1 Au1 125.30(9) . . ?
N1 C1 Au1 127.20(9) . . ?
C3 C2 N1 107.05(11) . . ?
C2 C3 N2 107.03(11) . . ?
C2 C3 C6 128.58(12) . . ?
N2 C3 C6 124.36(11) . . ?
O2 C6 O1 125.72(13) . . ?
O2 C6 C3 124.65(13) . . ?
O1 C6 C3 109.62(11) . . ?
O1 C7 C8 111.81(14) . . ?
Cl5 C9 Cl4 110.29(9) . . ?
Cl5 C9 Cl6 111.30(9) . . ?
Cl4 C9 Cl6 109.99(9) . . ?

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
C3 N2 C1 N1 0.42(15) . . . . ?
C5 N2 C1 N1 -179.89(12) . . . . ?
C3 N2 C1 Au1 -178.21(9) . . . . ?
C5 N2 C1 Au1 1.48(19) . . . . ?
C2 N1 C1 N2 -0.27(15) . . . . ?
C4 N1 C1 N2 178.75(13) . . . . ?
C2 N1 C1 Au1 178.33(10) . . . . ?
C4 N1 C1 Au1 -2.7(2) . . . . ?
C1 N1 C2 C3 0.01(15) . . . . ?
C4 N1 C2 C3 -179.03(13) . . . . ?
N1 C2 C3 N2 0.25(15) . . . . ?
N1 C2 C3 C6 178.01(13) . . . . ?
C1 N2 C3 C2 -0.42(15) . . . . ?
C5 N2 C3 C2 179.89(13) . . . . ?
C1 N2 C3 C6 -178.30(12) . . . . ?
C5 N2 C3 C6 2.0(2) . . . . ?
C7 O1 C6 O2 5.3(2) . . . . ?
C7 O1 C6 C3 -173.86(13) . . . . ?
C2 C3 C6 O2 -173.75(15) . . . . ?
N2 C3 C6 O2 3.7(2) . . . . ?
C2 C3 C6 O1 5.4(2) . . . . ?
N2 C3 C6 O1 -177.22(13) . . . . ?
C6 O1 C7 C8 -85.27(18) . . . . ?

_refine_diff_density_max         4.014
_refine_diff_density_min         -3.374
_refine_diff_density_rms         0.226

####################################################################### 
# 
# 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_sm24db
_database_code_depnum_ccdc_archive 'CCDC 2355438'
loop_
_audit_author_name
_audit_author_address
'Dirk Bockfeld'
;TU Braunschweig
Germany
;
_audit_update_record             
;
2024-05-14 deposited with the CCDC.	2024-07-30 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT110_sm24db              
;
PROBLEM: ADDSYM Detects Potential Lattice Translation ...          ? Check
RESPONSE: A significant number of reflection could not be indexed with the cell
 suggested by ADDSYMM (97% indexation with the given cell vs. 73 % indexation
 with the suggested smaller cell volume). Additionally, the two molecules are
 not exactly overlapping. The torsion angle f.e. of C6-O2-C7-C8 is 156.22 vs.
 C6A-O2A-C7A-C8A with 171.91.
;
_vrf_PLAT112_sm24db              
;
PROBLEM: ADDSYM Detects New (Pseudo) Symm. Elem         B        100 %Fit
RESPONSE: see above
;
_vrf_PLAT113_sm24db              
;
PROBLEM: ADDSYM Suggests Possible Pseudo/New  Space Group      P21/n Check
RESPONSE: see above
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H12 Au Cl N2 O2'
_chemical_formula_sum            'C8 H12 Au Cl N2 O2'
_chemical_formula_weight         400.61

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'
Cl Cl 0.1484 0.1585 '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'

_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                   17.5275(4)
_cell_length_b                   7.06271(17)
_cell_length_c                   17.9398(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.314(2)
_cell_angle_gamma                90
_cell_volume                     2207.33(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    39118
_cell_measurement_theta_min      2.2710
_cell_measurement_theta_max      38.5740

_exptl_crystal_description       irregular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.411
_exptl_crystal_F_000             1488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    13.548
_shelx_estimated_absorpt_T_min   0.344
_shelx_estimated_absorpt_T_max   0.613
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
9 -2 -24 0.0323
11 -9 -7 0.0466
-20 0 16 0.0418
-16 -4 17 0.0341
18 -6 -10 0.0409
20 0 -16 0.0371
24 0 -10 0.0437
-14 -2 -19 0.0401
0 0 -1 0.0233
0 0 1 0.0196
2 -6 20 0.0243
-3 10 6 0.0429
-1 4 -23 0.0365
2 0 1 0.0353
1 -1 1 0.0328
-1 -2 0 0.0468
-11 -2 23 0.0205
-24 -3 3 0.0375
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
8.6385 -1.9674 -23.9987 0.3826 -0.9239 0.0090
10.7742 -8.6994 -6.6517 0.3531 -0.4119 0.8401
-20.4939 0.4753 16.2993 -0.8526 0.5226 -0.0089
-16.3359 -4.3997 17.0841 -0.7408 0.4548 0.4944
18.2821 -5.9554 -9.8038 0.6897 -0.4219 0.5885
20.4939 -0.4753 -16.2993 0.8526 -0.5226 0.0089
23.6699 0.3672 -9.8094 0.9723 -0.2335 0.0089
-13.7488 -1.6557 -18.9151 -0.5197 -0.8480 -0.1037
-0.0002 -0.0008 -0.9999 0.0024 -0.0385 -0.0096
0.0002 0.0008 0.9999 -0.0024 0.0385 0.0096
1.6074 -6.0686 19.6874 -0.0492 0.6157 0.7865
-3.0739 9.5770 6.4882 -0.0361 0.4714 -0.8812
-0.9860 4.2088 -22.6537 0.0614 -0.7728 -0.6317
1.9980 0.0004 0.9987 0.0773 0.0499 0.0214
0.9961 -0.9991 1.0031 0.0266 0.0194 0.1121
-1.0049 -1.9993 0.0083 -0.0615 -0.0553 0.1874
-11.2264 -2.1383 23.0013 -0.5273 0.7682 0.3631
-23.8344 -2.6108 3.2139 -0.9867 -0.0774 0.1432
_exptl_absorpt_correction_T_min  0.413
_exptl_absorpt_correction_T_max  0.794
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.64a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.893
_oxdiff_exptl_absorpt_empirical_full_max 1.126
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            114486
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.284
_diffrn_reflns_theta_max         38.264
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             11729
_reflns_number_gt                9559
_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 1.171.42.64a (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.64a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.64a (Rigaku OD, 2022)'

_computing_structure_solution    
'SHELXT 2018/2 (G. M. Sheldrick, Acta Cryst., 2015, A71, 3-8)'
_computing_structure_refinement  
'SHELXL-2018/3 (G. M. Sheldrick, Acta Cryst., 2015, C71, 3-8)'
_computing_molecular_graphics    ?
_computing_publication_material  
'OLEX2 v1.3 (O. V. Dolomanov et al., J. Appl. Cryst., 2009, 42, 339-341)'

_refine_special_details          
;
 All H atoms were placed in idealised positions and refined using a riding
 model, with a common U restrained to be 1.2 (1.5 for methyl groups) times
 the equivalent isotropic displacement parameter of the parent atom.
 Ordered methyl groups were treated as rigid bodies and allowed to
 rotate around the E-CH3 bond.

 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0156P)²+2.6447P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         11729
_refine_ls_number_parameters     259
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0262
_refine_ls_wR_factor_ref         0.0460
_refine_ls_wR_factor_gt          0.0435
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.005
_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 0.26272(2) 0.15869(2) 0.48331(2) 0.01499(2) Uani 1 1 d . . . . .
Cl1 Cl 0.36861(3) 0.14830(8) 0.41942(3) 0.02042(10) Uani 1 1 d . . . . .
O1 O 0.09886(10) 0.0713(2) 0.75363(9) 0.0230(3) Uani 1 1 d . . . . .
O2 O -0.01790(9) 0.1025(2) 0.68839(9) 0.0192(3) Uani 1 1 d . . . . .
N1 N 0.09770(10) 0.2118(2) 0.50589(10) 0.0144(3) Uani 1 1 d . . . . .
N2 N 0.16274(10) 0.1195(2) 0.60839(10) 0.0149(3) Uani 1 1 d . . . . .
C1 C 0.16909(12) 0.1662(3) 0.53609(11) 0.0152(3) Uani 1 1 d . . . . .
C2 C 0.04622(12) 0.1938(3) 0.55738(11) 0.0157(3) Uani 1 1 d . . . . .
H2 H -0.007342 0.218389 0.549356 0.019 Uiso 1 1 calc R U . . .
C3 C 0.08647(11) 0.1338(3) 0.62256(11) 0.0144(3) Uani 1 1 d . . . . .
C4 C 0.07872(13) 0.2808(3) 0.42940(12) 0.0189(4) Uani 1 1 d . . . . .
H4A H 0.106711 0.398584 0.422699 0.028 Uiso 1 1 calc R U . . .
H4B H 0.023395 0.304603 0.420277 0.028 Uiso 1 1 calc R U . . .
H4C H 0.093301 0.185487 0.393874 0.028 Uiso 1 1 calc R U . . .
C5 C 0.22541(13) 0.0463(3) 0.66077(13) 0.0208(4) Uani 1 1 d . . . . .
H5A H 0.273342 0.050671 0.637387 0.031 Uiso 1 1 calc R U . . .
H5B H 0.214327 -0.084817 0.673802 0.031 Uiso 1 1 calc R U . . .
H5C H 0.230634 0.124046 0.706304 0.031 Uiso 1 1 calc R U . . .
C6 C 0.05902(13) 0.0986(3) 0.69548(12) 0.0167(4) Uani 1 1 d . . . . .
C7 C -0.05335(13) 0.0839(3) 0.75754(13) 0.0203(4) Uani 1 1 d . . . . .
H7A H -0.042515 0.197397 0.789350 0.024 Uiso 1 1 calc R U . . .
H7B H -0.032799 -0.028595 0.785914 0.024 Uiso 1 1 calc R U . . .
C8 C -0.13865(15) 0.0632(4) 0.73632(15) 0.0288(5) Uani 1 1 d . . . . .
H8A H -0.148983 -0.055606 0.708802 0.043 Uiso 1 1 calc R U . . .
H8B H -0.157507 0.169847 0.704554 0.043 Uiso 1 1 calc R U . . .
H8C H -0.164875 0.061731 0.781831 0.043 Uiso 1 1 calc R U . . .
Au1A Au 0.24306(2) 0.67522(2) 0.50943(2) 0.01526(2) Uani 1 1 d . . . . .
Cl1A Cl 0.12758(3) 0.66630(8) 0.55824(3) 0.02030(9) Uani 1 1 d . . . . .
O1A O 0.43082(11) 0.6068(3) 0.25709(9) 0.0267(4) Uani 1 1 d . . . . .
O2A O 0.54380(10) 0.6215(3) 0.33069(9) 0.0239(3) Uani 1 1 d . . . . .
N1A N 0.41268(10) 0.7251(2) 0.50328(10) 0.0148(3) Uani 1 1 d . . . . .
N2A N 0.35580(10) 0.6350(2) 0.39646(10) 0.0157(3) Uani 1 1 d . . . . .
C1A C 0.34298(12) 0.6794(3) 0.46730(11) 0.0146(3) Uani 1 1 d . . . . .
C2A C 0.46869(12) 0.7087(3) 0.45615(12) 0.0162(4) Uani 1 1 d . . . . .
H2A H 0.521904 0.733011 0.468326 0.019 Uiso 1 1 calc R U . . .
C3A C 0.43364(12) 0.6509(3) 0.38863(12) 0.0170(4) Uani 1 1 d . . . . .
C4A C 0.42480(13) 0.8014(3) 0.57911(12) 0.0193(4) Uani 1 1 d . . . . .
H4AA H 0.413940 0.937564 0.577845 0.029 Uiso 1 1 calc R U . . .
H4AB H 0.478210 0.780280 0.599854 0.029 Uiso 1 1 calc R U . . .
H4AC H 0.390418 0.737752 0.610643 0.029 Uiso 1 1 calc R U . . .
C5A C 0.29613(13) 0.5728(3) 0.33888(12) 0.0210(4) Uani 1 1 d . . . . .
H5AA H 0.309774 0.448628 0.319872 0.032 Uiso 1 1 calc R U . . .
H5AB H 0.291201 0.664501 0.297637 0.032 Uiso 1 1 calc R U . . .
H5AC H 0.247214 0.563345 0.360343 0.032 Uiso 1 1 calc R U . . .
C6A C 0.46705(13) 0.6239(3) 0.31799(13) 0.0193(4) Uani 1 1 d . . . . .
C7A C 0.58543(15) 0.6156(4) 0.26471(14) 0.0293(5) Uani 1 1 d . . . . .
H7AA H 0.590598 0.745005 0.244667 0.035 Uiso 1 1 calc R U . . .
H7AB H 0.557166 0.537026 0.225133 0.035 Uiso 1 1 calc R U . . .
C8A C 0.66322(14) 0.5325(4) 0.28727(15) 0.0271(5) Uani 1 1 d . . . . .
H8AA H 0.687057 0.596975 0.332297 0.041 Uiso 1 1 calc R U . . .
H8AB H 0.695412 0.548911 0.246397 0.041 Uiso 1 1 calc R U . . .
H8AC H 0.658052 0.397250 0.297849 0.041 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Au1 C1 1.984(2) . ?
Au1 Cl1 2.2873(5) . ?
O1 C6 1.205(3) . ?
O2 C6 1.341(3) . ?
O2 C7 1.453(3) . ?
N1 C1 1.347(3) . ?
N1 C2 1.366(3) . ?
N1 C4 1.460(3) . ?
N2 C1 1.355(3) . ?
N2 C3 1.392(3) . ?
N2 C5 1.459(3) . ?
C2 C3 1.365(3) . ?
C3 C6 1.464(3) . ?
C7 C8 1.509(3) . ?
Au1A C1A 1.982(2) . ?
Au1A Cl1A 2.2930(5) . ?
O1A C6A 1.208(3) . ?
O2A C6A 1.340(3) . ?
O2A C7A 1.458(3) . ?
N1A C1A 1.356(3) . ?
N1A C2A 1.369(3) . ?
N1A C4A 1.457(3) . ?
N2A C1A 1.352(3) . ?
N2A C3A 1.391(3) . ?
N2A C5A 1.455(3) . ?
C2A C3A 1.359(3) . ?
C3A C6A 1.466(3) . ?
C7A C8A 1.499(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 Cl1 178.42(6) . . ?
C6 O2 C7 115.91(17) . . ?
C1 N1 C2 111.04(17) . . ?
C1 N1 C4 124.31(17) . . ?
C2 N1 C4 124.57(18) . . ?
C1 N2 C3 109.81(17) . . ?
C1 N2 C5 124.58(18) . . ?
C3 N2 C5 125.32(17) . . ?
N1 C1 N2 105.84(17) . . ?
N1 C1 Au1 126.52(15) . . ?
N2 C1 Au1 127.58(15) . . ?
C3 C2 N1 106.89(18) . . ?
C2 C3 N2 106.40(17) . . ?
C2 C3 C6 128.94(19) . . ?
N2 C3 C6 124.59(19) . . ?
O1 C6 O2 124.5(2) . . ?
O1 C6 C3 125.8(2) . . ?
O2 C6 C3 109.73(18) . . ?
O2 C7 C8 107.35(19) . . ?
C1A Au1A Cl1A 179.28(6) . . ?
C6A O2A C7A 116.44(19) . . ?
C1A N1A C2A 110.82(17) . . ?
C1A N1A C4A 124.30(17) . . ?
C2A N1A C4A 124.54(18) . . ?
C1A N2A C3A 110.02(18) . . ?
C1A N2A C5A 123.84(18) . . ?
C3A N2A C5A 126.10(18) . . ?
N2A C1A N1A 105.57(17) . . ?
N2A C1A Au1A 126.88(16) . . ?
N1A C1A Au1A 127.54(15) . . ?
C3A C2A N1A 106.93(19) . . ?
C2A C3A N2A 106.65(18) . . ?
C2A C3A C6A 128.7(2) . . ?
N2A C3A C6A 124.5(2) . . ?
O1A C6A O2A 124.8(2) . . ?
O1A C6A C3A 125.1(2) . . ?
O2A C6A C3A 110.1(2) . . ?
O2A C7A C8A 108.3(2) . . ?

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
C2 N1 C1 N2 -0.4(2) . . . . ?
C4 N1 C1 N2 176.63(18) . . . . ?
C2 N1 C1 Au1 177.15(15) . . . . ?
C4 N1 C1 Au1 -5.8(3) . . . . ?
C3 N2 C1 N1 0.9(2) . . . . ?
C5 N2 C1 N1 174.99(19) . . . . ?
C3 N2 C1 Au1 -176.61(15) . . . . ?
C5 N2 C1 Au1 -2.5(3) . . . . ?
C1 N1 C2 C3 -0.3(2) . . . . ?
C4 N1 C2 C3 -177.27(19) . . . . ?
N1 C2 C3 N2 0.8(2) . . . . ?
N1 C2 C3 C6 177.8(2) . . . . ?
C1 N2 C3 C2 -1.1(2) . . . . ?
C5 N2 C3 C2 -175.11(19) . . . . ?
C1 N2 C3 C6 -178.27(19) . . . . ?
C5 N2 C3 C6 7.7(3) . . . . ?
C7 O2 C6 O1 4.0(3) . . . . ?
C7 O2 C6 C3 -175.54(17) . . . . ?
C2 C3 C6 O1 -168.9(2) . . . . ?
N2 C3 C6 O1 7.6(3) . . . . ?
C2 C3 C6 O2 10.6(3) . . . . ?
N2 C3 C6 O2 -172.81(18) . . . . ?
C6 O2 C7 C8 -171.91(19) . . . . ?
C3A N2A C1A N1A 0.7(2) . . . . ?
C5A N2A C1A N1A 178.46(18) . . . . ?
C3A N2A C1A Au1A -178.68(14) . . . . ?
C5A N2A C1A Au1A -0.9(3) . . . . ?
C2A N1A C1A N2A -0.4(2) . . . . ?
C4A N1A C1A N2A 173.27(18) . . . . ?
C2A N1A C1A Au1A 178.97(15) . . . . ?
C4A N1A C1A Au1A -7.4(3) . . . . ?
C1A N1A C2A C3A -0.1(2) . . . . ?
C4A N1A C2A C3A -173.69(19) . . . . ?
N1A C2A C3A N2A 0.5(2) . . . . ?
N1A C2A C3A C6A 175.8(2) . . . . ?
C1A N2A C3A C2A -0.7(2) . . . . ?
C5A N2A C3A C2A -178.45(19) . . . . ?
C1A N2A C3A C6A -176.27(19) . . . . ?
C5A N2A C3A C6A 6.0(3) . . . . ?
C7A O2A C6A O1A 6.0(3) . . . . ?
C7A O2A C6A C3A -173.75(19) . . . . ?
C2A C3A C6A O1A -165.3(2) . . . . ?
N2A C3A C6A O1A 9.2(4) . . . . ?
C2A C3A C6A O2A 14.4(3) . . . . ?
N2A C3A C6A O2A -171.06(19) . . . . ?
C6A O2A C7A C8A -156.2(2) . . . . ?

_refine_diff_density_max         1.755
_refine_diff_density_min         -1.499
_refine_diff_density_rms         0.172

####################################################################### 
# 
# 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_sm36db
_database_code_depnum_ccdc_archive 'CCDC 2355444'
loop_
_audit_author_name
_audit_author_address
'Dirk Bockfeld'
;TU Braunschweig
Germany
;
_audit_update_record             
;
2024-05-14 deposited with the CCDC.	2024-07-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H20 Au Cl2 N4 O4, C F3 O3 S'
_chemical_formula_sum            'C15 H20 Au Cl2 F3 N4 O7 S'
_chemical_formula_weight         725.28

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'
Cl Cl 0.1484 0.1585 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   9.84290(10)
_cell_length_b                   10.46050(10)
_cell_length_c                   12.6806(2)
_cell_angle_alpha                82.8460(10)
_cell_angle_beta                 85.0970(10)
_cell_angle_gamma                65.3480(10)
_cell_volume                     1176.57(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    52328
_cell_measurement_theta_min      2.2730
_cell_measurement_theta_max      34.3150

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.047
_exptl_crystal_F_000             700
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    6.635
_shelx_estimated_absorpt_T_min   0.350
_shelx_estimated_absorpt_T_max   0.692
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4 -4 16 0.0314
-9 6 -1 0.0950
4 4 -16 0.0353
9 -6 0 0.1052
7 10 14 0.0412
11 12 -3 0.0346
0 -2 -18 0.0344
-11 -13 0 0.0242
-13 -5 3 0.0538
14 5 0 0.0689
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-4.4160 -3.8249 15.8913 -0.0048 0.0207 0.9998
-8.7498 6.4368 -1.3945 0.1821 -0.9831 0.0209
3.9677 4.1456 -15.9412 0.0140 -0.0704 -0.9974
9.1030 -6.0775 -0.0018 -0.1810 0.9775 -0.1084
6.8867 9.8774 14.1134 -0.8878 -0.1641 0.4300
10.5828 12.3194 -3.2972 -0.7779 -0.1448 -0.6114
0.0291 -2.0000 -17.7826 0.4150 0.0759 -0.9067
-10.8418 -13.0412 -0.2939 0.8832 0.1641 0.4394
-13.4951 -5.0456 2.5733 0.6763 -0.5196 0.5222
13.7541 4.8396 -0.3118 -0.7250 0.5568 -0.4054
_exptl_absorpt_correction_T_min  0.272
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.64a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.683
_oxdiff_exptl_absorpt_empirical_full_max 1.668
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            16519
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.153
_diffrn_reflns_theta_max         32.585
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             16519
_reflns_number_gt                12792
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'CrysAlisPro 1.171.42.64a (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.64a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.64a (Rigaku OD, 2022)'

_computing_structure_solution    
'SHELXT 2018/2 (G. M. Sheldrick, Acta Cryst., 2015, A71, 3-8)'
_computing_structure_refinement  
'SHELXL-2018/3 (G. M. Sheldrick, Acta Cryst., 2015, C71, 3-8)'
_computing_molecular_graphics    ?
_computing_publication_material  
'OLEX2 v1.3 (O. V. Dolomanov et al., J. Appl. Cryst., 2009, 42, 339-341)'

_refine_special_details          
;
 All H atoms were placed in idealised positions and refined using a riding
 model, with a common U restrained to be 1.2 (1.5 for methyl groups) times
 the equivalent isotropic displacement parameter of the parent atom.
 Ordered methyl groups were treated as rigid bodies and allowed to 
 rotate around the E-CH3 bond.

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

 Refined as a 2-component twin. Component 2 rotated by -179.9751° 
 around [0.62 -0.78 -0.07] (reciprocal) or [0.71 -0.71 -0.00] (direct)
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1275P)²+11.7942P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         16519
_refine_ls_number_parameters     308
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0889
_refine_ls_R_factor_gt           0.0718
_refine_ls_wR_factor_ref         0.2122
_refine_ls_wR_factor_gt          0.2010
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 1.000000 1.000000 0.500000 0.01659(12) Uani 1 2 d S . P . .
Cl1 Cl 1.2027(3) 0.9630(3) 0.59334(19) 0.0249(4) Uani 1 1 d . . . . .
O1 O 0.6910(9) 0.8242(8) 0.8667(6) 0.0295(16) Uani 1 1 d . . . . .
O2 O 0.8621(8) 0.5991(7) 0.8872(6) 0.0240(14) Uani 1 1 d . . . . .
N1 N 0.8643(9) 0.8680(8) 0.6793(6) 0.0206(14) Uani 1 1 d . . . . .
N2 N 1.0544(9) 0.7057(8) 0.6058(6) 0.0218(15) Uani 1 1 d . . . . .
C1 C 0.9689(10) 0.8457(10) 0.6001(8) 0.0204(16) Uani 1 1 d . . . . .
C2 C 0.8871(10) 0.7386(9) 0.7373(7) 0.0206(16) Uani 1 1 d . . . . .
C3 C 1.0061(10) 0.6382(9) 0.6905(7) 0.0199(16) Uani 1 1 d . . . . .
H3 H 1.048145 0.539715 0.712240 0.024 Uiso 1 1 calc R U . . .
C4 C 0.7510(12) 1.0080(10) 0.7001(8) 0.028(2) Uani 1 1 d . . . . .
H4A H 0.652084 1.015401 0.684411 0.042 Uiso 1 1 calc R U . . .
H4B H 0.773064 1.080612 0.654927 0.042 Uiso 1 1 calc R U . . .
H4C H 0.752041 1.021784 0.775063 0.042 Uiso 1 1 calc R U . . .
C5 C 1.1802(10) 0.6350(10) 0.5323(8) 0.0235(18) Uani 1 1 d . . . . .
H5A H 1.259296 0.556637 0.571754 0.035 Uiso 1 1 calc R U . . .
H5B H 1.219484 0.702773 0.498550 0.035 Uiso 1 1 calc R U . . .
H5C H 1.145756 0.598265 0.477460 0.035 Uiso 1 1 calc R U . . .
C6 C 0.7998(11) 0.7285(10) 0.8361(8) 0.0213(17) Uani 1 1 d . . . . .
C7 C 0.7891(12) 0.5828(12) 0.9895(9) 0.033(2) Uani 1 1 d . . . . .
H7A H 0.684658 0.601708 0.979082 0.049 Uiso 1 1 calc R U . . .
H7B H 0.792531 0.649594 1.035869 0.049 Uiso 1 1 calc R U . . .
H7C H 0.840940 0.486019 1.022596 0.049 Uiso 1 1 calc R U . . .
Au1A Au 1.000000 1.000000 0.000000 0.01739(12) Uani 1 2 d S . P . .
Cl1A Cl 0.9342(3) 1.1918(3) 0.0921(2) 0.0279(5) Uani 1 1 d . . . . .
O1A O 0.8678(8) 0.6731(7) 0.3860(6) 0.0252(14) Uani 1 1 d . . . . .
O2A O 0.6240(8) 0.8221(8) 0.3892(6) 0.0243(14) Uani 1 1 d . . . . .
N1A N 0.8977(9) 0.8419(8) 0.1869(6) 0.0192(14) Uani 1 1 d . . . . .
N2A N 0.7127(8) 0.9958(8) 0.0973(6) 0.0205(14) Uani 1 1 d . . . . .
C1A C 0.8615(10) 0.9372(9) 0.1023(7) 0.0181(15) Uani 1 1 d . . . . .
C2A C 0.7652(10) 0.8457(10) 0.2410(7) 0.0200(16) Uani 1 1 d . . . . .
C3A C 0.6508(10) 0.9418(10) 0.1820(7) 0.0210(16) Uani 1 1 d . . . . .
H3A H 0.547115 0.966813 0.196880 0.025 Uiso 1 1 calc R U . . .
C4A C 1.0501(11) 0.7540(11) 0.2213(8) 0.027(2) Uani 1 1 d . . . . .
H4AA H 1.072234 0.654295 0.217197 0.040 Uiso 1 1 calc R U . . .
H4AB H 1.058609 0.768921 0.294793 0.040 Uiso 1 1 calc R U . . .
H4AC H 1.121265 0.780062 0.174894 0.040 Uiso 1 1 calc R U . . .
C5A C 0.6306(11) 1.1038(11) 0.0129(8) 0.0263(19) Uani 1 1 d . . . . .
H5AA H 0.655615 1.185433 0.011100 0.039 Uiso 1 1 calc R U . . .
H5AB H 0.522855 1.133598 0.027048 0.039 Uiso 1 1 calc R U . . .
H5AC H 0.658740 1.064218 -0.055870 0.039 Uiso 1 1 calc R U . . .
C6A C 0.7608(11) 0.7686(10) 0.3444(8) 0.0200(16) Uani 1 1 d . . . . .
C7A C 0.6041(12) 0.7629(12) 0.4961(8) 0.030(2) Uani 1 1 d . . . . .
H7AA H 0.598797 0.671990 0.493001 0.045 Uiso 1 1 calc R U . . .
H7AB H 0.511206 0.828026 0.529060 0.045 Uiso 1 1 calc R U . . .
H7AC H 0.688861 0.748790 0.538498 0.045 Uiso 1 1 calc R U . . .
S1 S 0.5047(3) 0.6058(3) 0.25808(19) 0.0226(4) Uani 1 1 d . . . . .
F1 F 0.5414(11) 0.4245(10) 0.1211(8) 0.055(2) Uani 1 1 d . . . . .
F2 F 0.3592(9) 0.4513(9) 0.2352(8) 0.052(2) Uani 1 1 d . . . . .
F3 F 0.5846(11) 0.3316(9) 0.2817(9) 0.062(3) Uani 1 1 d . . . . .
O3 O 0.4099(11) 0.7130(9) 0.1831(8) 0.042(2) Uani 1 1 d . . . . .
O4 O 0.4461(12) 0.6141(12) 0.3662(7) 0.044(2) Uani 1 1 d . . . . .
O5 O 0.6613(9) 0.5768(9) 0.2457(7) 0.0338(17) Uani 1 1 d . . . . .
C8 C 0.4959(13) 0.4443(12) 0.2240(10) 0.035(2) 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
Au1 C1 2.036(9) . ?
Au1 C1 2.036(9) 2_776 ?
Au1 Cl1 2.275(2) 2_776 ?
Au1 Cl1 2.275(2) . ?
O1 C6 1.196(11) . ?
O2 C6 1.336(11) . ?
O2 C7 1.455(11) . ?
N1 C1 1.343(12) . ?
N1 C2 1.396(11) . ?
N1 C4 1.464(12) . ?
N2 C1 1.347(11) . ?
N2 C3 1.372(12) . ?
N2 C5 1.470(11) . ?
C2 C3 1.355(12) . ?
C2 C6 1.477(13) . ?
Au1A C1A 2.050(8) 2_775 ?
Au1A C1A 2.050(8) . ?
Au1A Cl1A 2.276(2) . ?
Au1A Cl1A 2.276(2) 2_775 ?
O1A C6A 1.213(11) . ?
O2A C6A 1.330(12) . ?
O2A C7A 1.452(11) . ?
N1A C1A 1.333(11) . ?
N1A C2A 1.408(11) . ?
N1A C4A 1.465(12) . ?
N2A C1A 1.335(11) . ?
N2A C3A 1.366(12) . ?
N2A C5A 1.470(12) . ?
C2A C3A 1.361(13) . ?
C2A C6A 1.459(13) . ?
S1 O3 1.430(8) . ?
S1 O4 1.440(9) . ?
S1 O5 1.440(8) . ?
S1 C8 1.833(12) . ?
F1 C8 1.355(15) . ?
F2 C8 1.313(14) . ?
F3 C8 1.312(14) . ?

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 C1 180.0(5) . 2_776 ?
C1 Au1 Cl1 91.4(3) . 2_776 ?
C1 Au1 Cl1 88.6(3) 2_776 2_776 ?
C1 Au1 Cl1 88.6(3) . . ?
C1 Au1 Cl1 91.4(3) 2_776 . ?
Cl1 Au1 Cl1 180.0 2_776 . ?
C6 O2 C7 113.9(8) . . ?
C1 N1 C2 108.7(8) . . ?
C1 N1 C4 123.6(8) . . ?
C2 N1 C4 127.6(8) . . ?
C1 N2 C3 109.8(8) . . ?
C1 N2 C5 125.4(8) . . ?
C3 N2 C5 124.8(8) . . ?
N1 C1 N2 107.4(8) . . ?
N1 C1 Au1 125.1(7) . . ?
N2 C1 Au1 127.3(7) . . ?
C3 C2 N1 107.0(8) . . ?
C3 C2 C6 130.6(8) . . ?
N1 C2 C6 122.1(8) . . ?
C2 C3 N2 107.1(8) . . ?
O1 C6 O2 125.3(9) . . ?
O1 C6 C2 124.4(9) . . ?
O2 C6 C2 110.3(8) . . ?
C1A Au1A C1A 180.0 2_775 . ?
C1A Au1A Cl1A 91.7(3) 2_775 . ?
C1A Au1A Cl1A 88.3(3) . . ?
C1A Au1A Cl1A 88.3(3) 2_775 2_775 ?
C1A Au1A Cl1A 91.7(3) . 2_775 ?
Cl1A Au1A Cl1A 180.0 . 2_775 ?
C6A O2A C7A 117.0(8) . . ?
C1A N1A C2A 108.7(7) . . ?
C1A N1A C4A 125.5(8) . . ?
C2A N1A C4A 125.8(8) . . ?
C1A N2A C3A 110.0(8) . . ?
C1A N2A C5A 123.9(8) . . ?
C3A N2A C5A 126.1(8) . . ?
N1A C1A N2A 107.9(8) . . ?
N1A C1A Au1A 128.4(7) . . ?
N2A C1A Au1A 123.6(7) . . ?
C3A C2A N1A 106.0(8) . . ?
C3A C2A C6A 129.7(8) . . ?
N1A C2A C6A 124.0(8) . . ?
C2A C3A N2A 107.3(8) . . ?
O1A C6A O2A 124.5(9) . . ?
O1A C6A C2A 125.0(9) . . ?
O2A C6A C2A 110.4(8) . . ?
O3 S1 O4 114.5(6) . . ?
O3 S1 O5 115.6(6) . . ?
O4 S1 O5 114.7(6) . . ?
O3 S1 C8 103.3(6) . . ?
O4 S1 C8 102.4(6) . . ?
O5 S1 C8 103.9(5) . . ?
F3 C8 F2 108.9(11) . . ?
F3 C8 F1 106.7(11) . . ?
F2 C8 F1 107.4(10) . . ?
F3 C8 S1 111.9(9) . . ?
F2 C8 S1 111.7(8) . . ?
F1 C8 S1 109.9(9) . . ?

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
C2 N1 C1 N2 1.3(11) . . . . ?
C4 N1 C1 N2 179.1(9) . . . . ?
C2 N1 C1 Au1 -173.8(7) . . . . ?
C4 N1 C1 Au1 4.0(14) . . . . ?
C3 N2 C1 N1 -1.3(11) . . . . ?
C5 N2 C1 N1 178.5(9) . . . . ?
C3 N2 C1 Au1 173.7(7) . . . . ?
C5 N2 C1 Au1 -6.5(14) . . . . ?
C1 N1 C2 C3 -0.9(11) . . . . ?
C4 N1 C2 C3 -178.6(10) . . . . ?
C1 N1 C2 C6 173.9(9) . . . . ?
C4 N1 C2 C6 -3.8(15) . . . . ?
N1 C2 C3 N2 0.1(11) . . . . ?
C6 C2 C3 N2 -174.1(10) . . . . ?
C1 N2 C3 C2 0.8(11) . . . . ?
C5 N2 C3 C2 -179.0(9) . . . . ?
C7 O2 C6 O1 -2.5(15) . . . . ?
C7 O2 C6 C2 175.8(9) . . . . ?
C3 C2 C6 O1 -175.9(11) . . . . ?
N1 C2 C6 O1 10.7(16) . . . . ?
C3 C2 C6 O2 5.8(15) . . . . ?
N1 C2 C6 O2 -167.6(9) . . . . ?
C2A N1A C1A N2A -3.1(10) . . . . ?
C4A N1A C1A N2A -179.8(9) . . . . ?
C2A N1A C1A Au1A 172.7(7) . . . . ?
C4A N1A C1A Au1A -4.0(14) . . . . ?
C3A N2A C1A N1A 2.3(11) . . . . ?
C5A N2A C1A N1A -178.5(9) . . . . ?
C3A N2A C1A Au1A -173.8(6) . . . . ?
C5A N2A C1A Au1A 5.4(13) . . . . ?
C1A N1A C2A C3A 2.8(10) . . . . ?
C4A N1A C2A C3A 179.5(9) . . . . ?
C1A N1A C2A C6A -172.1(9) . . . . ?
C4A N1A C2A C6A 4.6(15) . . . . ?
N1A C2A C3A N2A -1.4(10) . . . . ?
C6A C2A C3A N2A 173.1(9) . . . . ?
C1A N2A C3A C2A -0.5(11) . . . . ?
C5A N2A C3A C2A -179.7(9) . . . . ?
C7A O2A C6A O1A 1.4(15) . . . . ?
C7A O2A C6A C2A -175.8(8) . . . . ?
C3A C2A C6A O1A 171.4(10) . . . . ?
N1A C2A C6A O1A -15.1(15) . . . . ?
C3A C2A C6A O2A -11.5(14) . . . . ?
N1A C2A C6A O2A 162.0(8) . . . . ?
O3 S1 C8 F3 176.3(10) . . . . ?
O4 S1 C8 F3 -64.5(11) . . . . ?
O5 S1 C8 F3 55.2(11) . . . . ?
O3 S1 C8 F2 -61.3(11) . . . . ?
O4 S1 C8 F2 57.9(11) . . . . ?
O5 S1 C8 F2 177.6(9) . . . . ?
O3 S1 C8 F1 57.9(10) . . . . ?
O4 S1 C8 F1 177.1(8) . . . . ?
O5 S1 C8 F1 -63.2(9) . . . . ?

_refine_diff_density_max         5.734
_refine_diff_density_min         -3.532
_refine_diff_density_rms         0.335

####################################################################### 
# 
# 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_sm37db
_database_code_depnum_ccdc_archive 'CCDC 2355440'
loop_
_audit_author_name
_audit_author_address
'Dirk Bockfeld'
;TU Braunschweig
Germany
;
_audit_update_record             
;
2024-05-14 deposited with the CCDC.	2024-07-30 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT084_sm37db              
;
PROBLEM: High wR2 Value (i.e. > 0.25) ................... 
RESPONSE: Despite several attempts only weakly diffracting crystals were
 obtained. The data quality is quite poor resulting in high R-values and low 
 Bond precision. This structure only confirms the connectivity of the compound. 
;
_vrf_PLAT342_sm37db              
;
PROBLEM: Low Bond Precision on  C-C Bonds ............... 
RESPONSE:  Despite several attempts only weakly diffracting crystals were
 obtained. The data quality is quite poor resulting in high R-values and low 
 Bond precision. This structure only confirms the connectivity of the compound.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H24 Au N4 O4, B F4'
_chemical_formula_sum            'C16 H24 Au B F4 N4 O4'
_chemical_formula_weight         620.17

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -4.4197 7.2980 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   7.0200(6)
_cell_length_b                   10.3525(10)
_cell_length_c                   15.2507(17)
_cell_angle_alpha                86.570(8)
_cell_angle_beta                 79.101(9)
_cell_angle_gamma                76.542(8)
_cell_volume                     1058.32(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6013
_cell_measurement_theta_min      8.6970
_cell_measurement_theta_max      73.4610

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.946
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    13.662
_shelx_estimated_absorpt_T_min   0.218
_shelx_estimated_absorpt_T_max   0.772
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
4 -1 -1 0.0551
-4 -1 0 0.0659
0 7 1 0.0459
0 -6 -1 0.0685
-1 0 -10 0.0080
1 0 10 0.0066
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
4.1971 -0.6395 -0.5082 -0.3866 0.5630 0.7305
-4.3992 -0.5743 0.3334 0.3056 -0.4455 -0.8415
0.0431 6.5242 1.0404 0.5185 -0.7529 0.4053
0.3459 -6.3606 -1.0518 -0.5365 0.7792 -0.3241
-0.9819 0.2167 -9.8451 -0.8238 -0.5668 -0.0089
0.9819 -0.2167 9.8451 0.8238 0.5668 0.0089
_exptl_absorpt_correction_T_min  0.246
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.64a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.303
_oxdiff_exptl_absorpt_empirical_full_max 3.146
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
- B-factor correction
;
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            10988
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.951
_diffrn_reflns_theta_max         75.012
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             10988
_reflns_number_gt                8123
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'CrysAlisPro 1.171.42.64a (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.64a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.64a (Rigaku OD, 2022)'

_computing_structure_solution    
'SHELXT 2018/2 (G. M. Sheldrick, Acta Cryst., 2015, A71, 3-8)'
_computing_structure_refinement  
'SHELXL-2018/3 (G. M. Sheldrick, Acta Cryst., 2015, C71, 3-8)'
_computing_molecular_graphics    ?
_computing_publication_material  
'OLEX2 v1.3 (O. V. Dolomanov et al., J. Appl. Cryst., 2009, 42, 339-341)'

_refine_special_details          
;
 All H atoms were placed in idealised positions and refined using a riding
 model, with a common U restrained to be 1.2 (1.5 for methyl groups) times
 the equivalent isotropic displacement parameter of the parent atom.
 Ordered methyl groups were treated as rigid bodies and allowed to 
 rotate around the E-CH3 bond.

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

 Refined as a 3-component twin. Component 2 rotated by 6.0221° 
 around [0.83 0.37 0.41] (reciprocal) or [1.00 0.05 0.02] (direct)
 Component 3 rotated by 1.8219° around [-0.18 -0.97 0.15] (reciprocal)
 or [-0.10 -0.99 0.12] (direct).

 The BF4 anion was found disordered and refined accordingly.

 This structure suffers from low bond length precision and exhibits high
 R values.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10988
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1674
_refine_ls_R_factor_gt           0.1326
_refine_ls_wR_factor_ref         0.3902
_refine_ls_wR_factor_gt          0.3468
_refine_ls_goodness_of_fit_ref   1.613
_refine_ls_restrained_S_all      1.613
_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 0.25474(12) 0.57491(9) 0.46332(7) 0.0536(5) Uani 1 1 d . . . . .
O1 O 0.585(3) 0.560(2) 0.0802(15) 0.074(5) Uani 1 1 d . . . . .
O2 O 0.471(3) 0.7783(19) 0.0518(13) 0.062(4) Uani 1 1 d . . . . .
O3 O -0.057(3) 0.551(2) 0.8535(14) 0.072(5) Uani 1 1 d . . . . .
O4 O 0.032(3) 0.3286(18) 0.8613(13) 0.059(4) Uani 1 1 d . . . . .
N1 N 0.402(3) 0.609(2) 0.2662(14) 0.052(4) Uani 1 1 d . . . . .
N2 N 0.271(3) 0.801(3) 0.3256(17) 0.068(6) Uani 1 1 d . . . . .
N3 N 0.104(3) 0.528(2) 0.6602(16) 0.059(5) Uani 1 1 d . . . . .
N4 N 0.232(3) 0.346(2) 0.5923(14) 0.058(5) Uani 1 1 d . . . . .
C1 C 0.315(4) 0.671(2) 0.3434(17) 0.057(5) Uani 1 1 d . . . . .
C2 C 0.412(4) 0.706(3) 0.1988(18) 0.061(6) Uani 1 1 d . . . . .
C3 C 0.326(4) 0.827(2) 0.2381(17) 0.055(5) Uani 1 1 d . . . . .
H3 H 0.309405 0.912254 0.209254 0.066 Uiso 1 1 calc R U . . .
C4 C 0.468(4) 0.469(2) 0.255(2) 0.061(6) Uani 1 1 d . . . . .
H4A H 0.373679 0.436888 0.226252 0.091 Uiso 1 1 calc R U . . .
H4B H 0.474449 0.424941 0.313034 0.091 Uiso 1 1 calc R U . . .
H4C H 0.599826 0.449032 0.216791 0.091 Uiso 1 1 calc R U . . .
C5 C 0.172(5) 0.902(3) 0.395(2) 0.073(8) Uani 1 1 d . . . . .
H5A H 0.134817 0.856655 0.451768 0.109 Uiso 1 1 calc R U . . .
H5B H 0.052603 0.957708 0.376773 0.109 Uiso 1 1 calc R U . . .
H5C H 0.263892 0.957101 0.402089 0.109 Uiso 1 1 calc R U . . .
C6 C 0.499(4) 0.670(3) 0.105(2) 0.058(6) Uani 1 1 d . . . . .
C7 C 0.544(4) 0.752(3) -0.0439(18) 0.064(6) Uani 1 1 d . . . . .
H7A H 0.684800 0.702568 -0.053724 0.077 Uiso 1 1 calc R U . . .
H7B H 0.464413 0.696964 -0.065722 0.077 Uiso 1 1 calc R U . . .
C8 C 0.524(5) 0.880(3) -0.092(2) 0.071(7) Uani 1 1 d . . . . .
H8A H 0.568862 0.865012 -0.156268 0.107 Uiso 1 1 calc R U . . .
H8B H 0.606151 0.932407 -0.071179 0.107 Uiso 1 1 calc R U . . .
H8C H 0.384493 0.928640 -0.080911 0.107 Uiso 1 1 calc R U . . .
C9 C 0.194(4) 0.472(2) 0.5794(15) 0.053(5) Uani 1 1 d . . . . .
C10 C 0.092(3) 0.424(2) 0.7242(17) 0.053(5) Uani 1 1 d . . . . .
C11 C 0.174(4) 0.311(3) 0.680(2) 0.071(7) Uani 1 1 d . . . . .
H11 H 0.189640 0.223117 0.704245 0.085 Uiso 1 1 calc R U . . .
C12 C 0.027(4) 0.671(3) 0.677(2) 0.070(7) Uani 1 1 d . . . . .
H12A H 0.134370 0.708760 0.689946 0.105 Uiso 1 1 calc R U . . .
H12B H -0.082518 0.683360 0.728349 0.105 Uiso 1 1 calc R U . . .
H12C H -0.020502 0.715116 0.624245 0.105 Uiso 1 1 calc R U . . .
C13 C 0.339(4) 0.248(3) 0.518(2) 0.071(7) Uani 1 1 d . . . . .
H13A H 0.249087 0.245435 0.476471 0.106 Uiso 1 1 calc R U . . .
H13B H 0.380422 0.159761 0.543847 0.106 Uiso 1 1 calc R U . . .
H13C H 0.456896 0.277422 0.485349 0.106 Uiso 1 1 calc R U . . .
C14 C 0.012(4) 0.445(3) 0.8208(18) 0.058(6) Uani 1 1 d . . . . .
C15 C -0.036(4) 0.330(3) 0.960(2) 0.065(6) Uani 1 1 d . . . . .
H15A H 0.041185 0.378538 0.988654 0.077 Uiso 1 1 calc R U . . .
H15B H -0.178635 0.373505 0.975048 0.077 Uiso 1 1 calc R U . . .
C16 C -0.001(4) 0.189(3) 0.990(2) 0.073(7) Uani 1 1 d . . . . .
H16A H -0.085332 0.143917 0.964511 0.109 Uiso 1 1 calc R U . . .
H16B H -0.034822 0.184928 1.055564 0.109 Uiso 1 1 calc R U . . .
H16C H 0.139050 0.145618 0.970816 0.109 Uiso 1 1 calc R U . . .
F1 F 0.283(3) 0.913(2) 0.6032(15) 0.101(7) Uani 1 1 d . . . . .
B1 B 0.348(7) 0.912(4) 0.687(3) 0.087(11) Uani 1 1 d . . . . .
F2 F 0.435(10) 0.800(3) 0.700(3) 0.10(2) Uani 0.55(6) 1 d . . P A 1
F3 F 0.150(6) 0.959(6) 0.741(3) 0.103(18) Uani 0.55(6) 1 d . . P A 1
F4 F 0.437(8) 1.016(7) 0.688(5) 0.092(17) Uani 0.55(6) 1 d . . P A 1
F2A F 0.562(7) 0.833(5) 0.676(3) 0.077(14) Uani 0.45(6) 1 d . . P A 2
F3A F 0.257(8) 0.843(5) 0.760(3) 0.084(19) Uani 0.45(6) 1 d . . P A 2
F4A F 0.356(11) 1.026(5) 0.709(7) 0.10(2) Uani 0.45(6) 1 d . . P A 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 C9 2.03(2) . ?
Au1 C1 2.05(2) . ?
O1 C6 1.20(3) . ?
O2 C6 1.34(3) . ?
O2 C7 1.47(3) . ?
O3 C14 1.19(3) . ?
O4 C14 1.31(3) . ?
O4 C15 1.49(3) . ?
N1 C1 1.34(3) . ?
N1 C2 1.39(4) . ?
N1 C4 1.43(3) . ?
N2 C1 1.33(3) . ?
N2 C3 1.35(4) . ?
N2 C5 1.48(4) . ?
N3 C9 1.37(3) . ?
N3 C10 1.41(3) . ?
N3 C12 1.47(4) . ?
N4 C9 1.28(3) . ?
N4 C11 1.37(4) . ?
N4 C13 1.53(3) . ?
C2 C3 1.38(3) . ?
C2 C6 1.48(4) . ?
C7 C8 1.47(4) . ?
C10 C11 1.34(4) . ?
C10 C14 1.48(4) . ?
C15 C16 1.48(4) . ?
F1 B1 1.44(5) . ?
B1 F2 1.20(6) . ?
B1 F4A 1.27(7) . ?
B1 F4 1.37(7) . ?
B1 F3A 1.41(6) . ?
B1 F3 1.47(6) . ?
B1 F2A 1.51(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
C9 Au1 C1 177.5(9) . . ?
C6 O2 C7 114(2) . . ?
C14 O4 C15 116(2) . . ?
C1 N1 C2 108(2) . . ?
C1 N1 C4 126(2) . . ?
C2 N1 C4 126(2) . . ?
C1 N2 C3 111(2) . . ?
C1 N2 C5 123(3) . . ?
C3 N2 C5 126(3) . . ?
C9 N3 C10 108(2) . . ?
C9 N3 C12 126(2) . . ?
C10 N3 C12 126(2) . . ?
C9 N4 C11 113(2) . . ?
C9 N4 C13 123(2) . . ?
C11 N4 C13 125(2) . . ?
N2 C1 N1 108(2) . . ?
N2 C1 Au1 128(2) . . ?
N1 C1 Au1 124.1(18) . . ?
C3 C2 N1 107(2) . . ?
C3 C2 C6 131(3) . . ?
N1 C2 C6 122(2) . . ?
N2 C3 C2 106(2) . . ?
O1 C6 O2 125(3) . . ?
O1 C6 C2 125(3) . . ?
O2 C6 C2 110(2) . . ?
C8 C7 O2 108(2) . . ?
N4 C9 N3 106(2) . . ?
N4 C9 Au1 128.1(17) . . ?
N3 C9 Au1 125.5(18) . . ?
C11 C10 N3 106(2) . . ?
C11 C10 C14 130(3) . . ?
N3 C10 C14 124(2) . . ?
C10 C11 N4 106(3) . . ?
O3 C14 O4 128(3) . . ?
O3 C14 C10 124(3) . . ?
O4 C14 C10 108(2) . . ?
C16 C15 O4 106(2) . . ?
F2 B1 F4 121(5) . . ?
F4A B1 F3A 111(6) . . ?
F2 B1 F1 107(4) . . ?
F4A B1 F1 113(6) . . ?
F4 B1 F1 109(5) . . ?
F3A B1 F1 118(3) . . ?
F2 B1 F3 118(5) . . ?
F4 B1 F3 103(4) . . ?
F1 B1 F3 96(4) . . ?
F4A B1 F2A 104(5) . . ?
F3A B1 F2A 101(4) . . ?
F1 B1 F2A 108(3) . . ?

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
C3 N2 C1 N1 0(3) . . . . ?
C5 N2 C1 N1 179(3) . . . . ?
C3 N2 C1 Au1 -177(2) . . . . ?
C5 N2 C1 Au1 2(4) . . . . ?
C2 N1 C1 N2 1(3) . . . . ?
C4 N1 C1 N2 -178(2) . . . . ?
C2 N1 C1 Au1 177.7(18) . . . . ?
C4 N1 C1 Au1 -1(4) . . . . ?
C1 N1 C2 C3 -1(3) . . . . ?
C4 N1 C2 C3 178(2) . . . . ?
C1 N1 C2 C6 -180(2) . . . . ?
C4 N1 C2 C6 -1(4) . . . . ?
C1 N2 C3 C2 -1(3) . . . . ?
C5 N2 C3 C2 180(3) . . . . ?
N1 C2 C3 N2 1(3) . . . . ?
C6 C2 C3 N2 180(3) . . . . ?
C7 O2 C6 O1 3(4) . . . . ?
C7 O2 C6 C2 -177(2) . . . . ?
C3 C2 C6 O1 174(3) . . . . ?
N1 C2 C6 O1 -8(4) . . . . ?
C3 C2 C6 O2 -6(4) . . . . ?
N1 C2 C6 O2 173(2) . . . . ?
C6 O2 C7 C8 -173(2) . . . . ?
C11 N4 C9 N3 -1(3) . . . . ?
C13 N4 C9 N3 -178(2) . . . . ?
C11 N4 C9 Au1 178.7(19) . . . . ?
C13 N4 C9 Au1 2(4) . . . . ?
C10 N3 C9 N4 1(3) . . . . ?
C12 N3 C9 N4 -178(2) . . . . ?
C10 N3 C9 Au1 -178.9(17) . . . . ?
C12 N3 C9 Au1 2(4) . . . . ?
C9 N3 C10 C11 -1(3) . . . . ?
C12 N3 C10 C11 178(2) . . . . ?
C9 N3 C10 C14 177(2) . . . . ?
C12 N3 C10 C14 -4(4) . . . . ?
N3 C10 C11 N4 0(3) . . . . ?
C14 C10 C11 N4 -177(2) . . . . ?
C9 N4 C11 C10 1(3) . . . . ?
C13 N4 C11 C10 178(2) . . . . ?
C15 O4 C14 O3 -1(4) . . . . ?
C15 O4 C14 C10 178.5(18) . . . . ?
C11 C10 C14 O3 180(3) . . . . ?
N3 C10 C14 O3 3(4) . . . . ?
C11 C10 C14 O4 0(4) . . . . ?
N3 C10 C14 O4 -177(2) . . . . ?
C14 O4 C15 C16 179(2) . . . . ?

_refine_diff_density_max         7.325
_refine_diff_density_min         -3.611
_refine_diff_density_rms         0.357

####################################################################### 
# 
# 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_sm34db
_database_code_depnum_ccdc_archive 'CCDC 2355441'
loop_
_audit_author_name
_audit_author_address
'Dirk Bockfeld'
;TU Braunschweig
Germany
;
_audit_update_record             
;
2024-05-14 deposited with the CCDC.	2024-07-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H8 Au Cl3 N2 O2'
_chemical_formula_sum            'C6 H8 Au Cl3 N2 O2'
_chemical_formula_weight         443.46

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'
Cl Cl 0.1484 0.1585 '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'

_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                   10.7651(2)
_cell_length_b                   10.9548(2)
_cell_length_c                   11.9269(2)
_cell_angle_alpha                66.2328(18)
_cell_angle_beta                 83.8452(16)
_cell_angle_gamma                62.158(2)
_cell_volume                     1132.52(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    73807
_cell_measurement_theta_min      2.2890
_cell_measurement_theta_max      44.9620

_exptl_crystal_description       irregular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.601
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    13.673
_shelx_estimated_absorpt_T_min   0.138
_shelx_estimated_absorpt_T_max   0.408
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-13 -14 -4 0.0959
5 3 16 0.0726
-1 0 -15 0.0665
-12 -14 -9 0.0977
-9 -3 11 0.0541
-6 1 14 0.0509
7 0 -14 0.0472
-6 -15 -10 0.1055
-12 0 8 0.0374
13 1 -7 0.0414
12 0 -8 0.0404
9 -7 -1 0.0798
-9 7 1 0.0950
14 2 1 0.0548
-13 -1 -5 0.0548
14 5 6 0.0633
13 1 5 0.0637
-1 -7 10 0.0861
-7 -1 -13 0.0660
-10 0 11 0.0357
9 -1 -12 0.0364
13 14 4 0.0874
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-12.5901 -13.5654 -4.2989 0.0008 -0.0091 1.0000
4.8278 3.3220 15.5490 -0.1767 0.9546 -0.2399
-1.3915 0.4407 -14.8207 0.1821 -0.9826 -0.0376
-11.8454 -13.6778 -8.5580 0.1333 -0.2473 0.9597
-9.3882 -3.2599 11.4305 -0.6211 0.5888 0.5172
-6.4241 0.8372 14.3176 -0.7022 0.6661 0.2514
7.3422 0.3478 -13.6013 0.6847 -0.6494 -0.3309
-5.7821 -15.0963 -9.7123 0.5877 -0.0783 0.8053
-12.3309 -0.0935 7.5241 -0.8775 0.1151 0.4655
12.9160 1.3322 -6.7955 0.8372 -0.1097 -0.5357
12.2424 -0.0801 -7.6223 0.8827 -0.1158 -0.4554
8.5888 -6.8637 -1.3994 0.8788 0.4771 -0.0092
-8.5888 6.8637 1.3994 -0.8788 -0.4771 0.0092
14.0729 1.8542 1.1657 0.7264 0.3951 -0.5623
-12.8516 -1.2537 -5.2004 -0.6050 -0.6383 0.4760
14.2039 4.6524 5.5108 0.5120 0.5407 -0.6675
12.6778 0.9102 5.1537 0.6125 0.6461 -0.4554
-0.5678 -7.0386 9.8923 0.1219 0.9223 0.3668
-6.8866 -0.6969 -12.8874 -0.1274 -0.9693 0.2105
-10.3536 -0.2166 10.9574 -0.8198 0.3916 0.4177
9.4642 -1.1673 -11.8056 0.8514 -0.4066 -0.3313
12.6259 13.5116 4.0606 0.0086 -0.0022 -1.0000
_exptl_absorpt_correction_T_min  0.113
_exptl_absorpt_correction_T_max  0.724
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.64a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.755
_oxdiff_exptl_absorpt_empirical_full_max 1.654
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            41473
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.150
_diffrn_reflns_theta_max         45.023
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             41473
_reflns_number_gt                33178
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'CrysAlisPro 1.171.42.64a (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.64a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.64a (Rigaku OD, 2022)'

_computing_structure_solution    
'SHELXT 2018/2 (G. M. Sheldrick, Acta Cryst., 2015, A71, 3-8)'
_computing_structure_refinement  
'SHELXL-2018/3 (G. M. Sheldrick, Acta Cryst., 2015, C71, 3-8)'
_computing_molecular_graphics    ?
_computing_publication_material  
'OLEX2 v1.3 (O. V. Dolomanov et al., J. Appl. Cryst., 2009, 42, 339-341)'

_refine_special_details          
;
 The OH hydrogen atoms H2 and H2A were refined freely.
 All other H atoms were placed in idealised positions and refined using a riding
 model, with a common U restrained to be 1.2 (1.5 for methyl groups) times
 the equivalent isotropic displacement parameter of the parent atom.
 Ordered methyl groups were treated as rigid bodies and allowed to
 rotate around the E-CH3 bond.

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

 Refined as a 2-component twin. Component 2 rotated by 179.9923°
 around [0.39 0.84 0.37] (reciprocal) or [0.00 1.00 0.00] (direct).
;
_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+0.5441P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         41473
_refine_ls_number_parameters     266
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0267
_refine_ls_wR_factor_ref         0.0688
_refine_ls_wR_factor_gt          0.0652
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_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 1.02305(2) 0.44925(2) 0.32115(2) 0.01474(2) Uani 1 1 d . . . . .
Cl1 Cl 1.24631(6) 0.28200(7) 0.42585(6) 0.02345(10) Uani 1 1 d . . . . .
Cl2 Cl 1.00135(7) 0.26831(6) 0.28730(6) 0.02290(10) Uani 1 1 d . . . . .
Cl3 Cl 1.02722(7) 0.64620(7) 0.34005(7) 0.02625(11) Uani 1 1 d . . . . .
O1 O 0.40452(17) 0.7310(2) 0.32915(16) 0.0200(3) Uani 1 1 d . . . . .
O2 O 0.35969(18) 0.8745(2) 0.12541(16) 0.0203(3) Uani 1 1 d . . . . .
N1 N 0.70717(18) 0.6045(2) 0.29102(17) 0.0151(3) Uani 1 1 d . . . . .
N2 N 0.79115(19) 0.6978(2) 0.12291(18) 0.0175(3) Uani 1 1 d . . . . .
C1 C 0.8267(2) 0.5927(2) 0.23962(19) 0.0153(3) Uani 1 1 d . . . . .
C2 C 0.5936(2) 0.7199(2) 0.20490(19) 0.0153(3) Uani 1 1 d . . . . .
C3 C 0.6475(2) 0.7772(2) 0.0993(2) 0.0178(3) Uani 1 1 d . . . . .
H3 H 0.595222 0.856869 0.024053 0.021 Uiso 1 1 calc R U . . .
C4 C 0.7000(3) 0.5059(3) 0.4163(2) 0.0214(4) Uani 1 1 d . . . . .
H4A H 0.669915 0.562093 0.468959 0.032 Uiso 1 1 calc R U . . .
H4B H 0.793376 0.419004 0.449352 0.032 Uiso 1 1 calc R U . . .
H4C H 0.631968 0.470749 0.414181 0.032 Uiso 1 1 calc R U . . .
C5 C 0.8909(3) 0.7244(3) 0.0343(2) 0.0249(4) Uani 1 1 d . . . . .
H5A H 0.927131 0.782158 0.052603 0.037 Uiso 1 1 calc R U . . .
H5B H 0.842536 0.781304 -0.049301 0.037 Uiso 1 1 calc R U . . .
H5C H 0.969591 0.627549 0.040346 0.037 Uiso 1 1 calc R U . . .
C6 C 0.4449(2) 0.7733(2) 0.22748(19) 0.0157(3) Uani 1 1 d . . . . .
Au1A Au 0.47588(2) 0.28917(2) 0.18480(2) 0.01499(2) Uani 1 1 d . . . . .
Cl1A Cl 0.25068(6) 0.43765(7) 0.08255(6) 0.02450(10) Uani 1 1 d . . . . .
Cl2A Cl 0.47507(7) 0.07075(7) 0.21131(6) 0.02450(10) Uani 1 1 d . . . . .
Cl3A Cl 0.49723(8) 0.49189(7) 0.17080(7) 0.03086(14) Uani 1 1 d . . . . .
O1A O 1.09166(17) -0.0286(2) 0.16821(15) 0.0197(3) Uani 1 1 d . . . . .
O2A O 1.14029(17) -0.1352(2) 0.37472(15) 0.0189(3) Uani 1 1 d . . . . .
N1A N 0.79096(19) 0.1179(2) 0.20799(17) 0.0158(3) Uani 1 1 d . . . . .
N2A N 0.71214(19) 0.0908(2) 0.38747(17) 0.0162(3) Uani 1 1 d . . . . .
C1A C 0.6735(2) 0.1590(2) 0.26554(19) 0.0158(3) Uani 1 1 d . . . . .
C2A C 0.9064(2) 0.0201(2) 0.29695(19) 0.0151(3) Uani 1 1 d . . . . .
C3A C 0.8554(2) 0.0041(2) 0.40882(19) 0.0164(3) Uani 1 1 d . . . . .
H3A H 0.909313 -0.056084 0.486919 0.020 Uiso 1 1 calc R U . . .
C4A C 0.7937(3) 0.1724(3) 0.0740(2) 0.0265(5) Uani 1 1 d . . . . .
H4AA H 0.830980 0.245023 0.046162 0.040 Uiso 1 1 calc R U . . .
H4AB H 0.697743 0.221451 0.034490 0.040 Uiso 1 1 calc R U . . .
H4AC H 0.854318 0.087185 0.051832 0.040 Uiso 1 1 calc R U . . .
C5A C 0.6145(2) 0.1086(3) 0.4820(2) 0.0219(4) Uani 1 1 d . . . . .
H5AA H 0.582619 0.207673 0.483429 0.033 Uiso 1 1 calc R U . . .
H5AB H 0.662731 0.029547 0.562676 0.033 Uiso 1 1 calc R U . . .
H5AC H 0.532843 0.100647 0.463280 0.033 Uiso 1 1 calc R U . . .
C6A C 1.0545(2) -0.0492(2) 0.2718(2) 0.0156(3) Uani 1 1 d . . . . .
H2A H 1.217(5) -0.174(5) 0.357(4) 0.032(11) Uiso 1 1 d . . . . .
H2 H 0.274(5) 0.903(5) 0.145(4) 0.036(11) 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 1.997(2) . ?
Au1 Cl3 2.2787(6) . ?
Au1 Cl2 2.2900(6) . ?
Au1 Cl1 2.3192(6) . ?
O1 C6 1.223(3) . ?
O2 C6 1.324(3) . ?
N1 C1 1.337(3) . ?
N1 C2 1.388(3) . ?
N1 C4 1.469(3) . ?
N2 C1 1.349(3) . ?
N2 C3 1.367(3) . ?
N2 C5 1.468(3) . ?
C2 C3 1.365(3) . ?
C2 C6 1.462(3) . ?
Au1A C1A 1.997(2) . ?
Au1A Cl3A 2.2764(6) . ?
Au1A Cl2A 2.2879(6) . ?
Au1A Cl1A 2.3155(6) . ?
O1A C6A 1.221(3) . ?
O2A C6A 1.321(3) . ?
N1A C1A 1.343(3) . ?
N1A C2A 1.393(3) . ?
N1A C4A 1.466(3) . ?
N2A C1A 1.345(3) . ?
N2A C3A 1.366(3) . ?
N2A C5A 1.465(3) . ?
C2A C3A 1.363(3) . ?
C2A C6A 1.469(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Au1 Cl3 87.23(6) . . ?
C1 Au1 Cl2 87.56(6) . . ?
Cl3 Au1 Cl2 174.44(2) . . ?
C1 Au1 Cl1 176.95(6) . . ?
Cl3 Au1 Cl1 92.14(2) . . ?
Cl2 Au1 Cl1 93.17(2) . . ?
C1 N1 C2 108.65(17) . . ?
C1 N1 C4 124.76(17) . . ?
C2 N1 C4 126.54(18) . . ?
C1 N2 C3 109.70(18) . . ?
C1 N2 C5 125.51(19) . . ?
C3 N2 C5 124.79(19) . . ?
N1 C1 N2 107.70(17) . . ?
N1 C1 Au1 126.48(15) . . ?
N2 C1 Au1 125.80(15) . . ?
C3 C2 N1 107.26(17) . . ?
C3 C2 C6 127.23(19) . . ?
N1 C2 C6 125.44(18) . . ?
C2 C3 N2 106.70(18) . . ?
O1 C6 O2 124.25(19) . . ?
O1 C6 C2 123.75(19) . . ?
O2 C6 C2 111.99(18) . . ?
C1A Au1A Cl3A 88.00(6) . . ?
C1A Au1A Cl2A 86.40(6) . . ?
Cl3A Au1A Cl2A 174.30(2) . . ?
C1A Au1A Cl1A 177.14(6) . . ?
Cl3A Au1A Cl1A 92.92(2) . . ?
Cl2A Au1A Cl1A 92.72(2) . . ?
C1A N1A C2A 108.31(18) . . ?
C1A N1A C4A 124.61(19) . . ?
C2A N1A C4A 127.06(18) . . ?
C1A N2A C3A 109.61(17) . . ?
C1A N2A C5A 124.74(18) . . ?
C3A N2A C5A 125.64(18) . . ?
N1A C1A N2A 107.91(18) . . ?
N1A C1A Au1A 125.98(16) . . ?
N2A C1A Au1A 126.03(15) . . ?
C3A C2A N1A 107.10(18) . . ?
C3A C2A C6A 127.54(19) . . ?
N1A C2A C6A 125.35(18) . . ?
C2A C3A N2A 107.07(18) . . ?
O1A C6A O2A 125.06(19) . . ?
O1A C6A C2A 123.51(19) . . ?
O2A C6A C2A 111.43(18) . . ?

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
C2 N1 C1 N2 -0.1(2) . . . . ?
C4 N1 C1 N2 177.4(2) . . . . ?
C2 N1 C1 Au1 178.49(15) . . . . ?
C4 N1 C1 Au1 -4.0(3) . . . . ?
C3 N2 C1 N1 -0.2(3) . . . . ?
C5 N2 C1 N1 179.4(2) . . . . ?
C3 N2 C1 Au1 -178.85(16) . . . . ?
C5 N2 C1 Au1 0.7(3) . . . . ?
C1 N1 C2 C3 0.4(2) . . . . ?
C4 N1 C2 C3 -177.1(2) . . . . ?
C1 N1 C2 C6 -176.6(2) . . . . ?
C4 N1 C2 C6 5.9(3) . . . . ?
N1 C2 C3 N2 -0.6(2) . . . . ?
C6 C2 C3 N2 176.4(2) . . . . ?
C1 N2 C3 C2 0.5(3) . . . . ?
C5 N2 C3 C2 -179.1(2) . . . . ?
C3 C2 C6 O1 -169.2(2) . . . . ?
N1 C2 C6 O1 7.3(4) . . . . ?
C3 C2 C6 O2 9.6(3) . . . . ?
N1 C2 C6 O2 -173.9(2) . . . . ?
C2A N1A C1A N2A 0.4(2) . . . . ?
C4A N1A C1A N2A -177.9(2) . . . . ?
C2A N1A C1A Au1A -176.51(15) . . . . ?
C4A N1A C1A Au1A 5.1(3) . . . . ?
C3A N2A C1A N1A -0.5(3) . . . . ?
C5A N2A C1A N1A 179.1(2) . . . . ?
C3A N2A C1A Au1A 176.42(16) . . . . ?
C5A N2A C1A Au1A -4.0(3) . . . . ?
C1A N1A C2A C3A -0.2(2) . . . . ?
C4A N1A C2A C3A 178.1(2) . . . . ?
C1A N1A C2A C6A -179.4(2) . . . . ?
C4A N1A C2A C6A -1.1(4) . . . . ?
N1A C2A C3A N2A -0.1(2) . . . . ?
C6A C2A C3A N2A 179.1(2) . . . . ?
C1A N2A C3A C2A 0.4(2) . . . . ?
C5A N2A C3A C2A -179.2(2) . . . . ?
C3A C2A C6A O1A -179.8(2) . . . . ?
N1A C2A C6A O1A -0.7(3) . . . . ?
C3A C2A C6A O2A 0.1(3) . . . . ?
N1A C2A C6A O2A 179.2(2) . . . . ?

_refine_diff_density_max         2.950
_refine_diff_density_min         -1.297
_refine_diff_density_rms         0.175

####################################################################### 
# 
# 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_sm01rfdb
_database_code_depnum_ccdc_archive 'CCDC 2355437'
loop_
_audit_author_name
_audit_author_address
'Dirk Bockfeld'
;TU Braunschweig
Germany
;
_audit_update_record             
;
2024-05-14 deposited with the CCDC.	2024-07-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H10 Au Cl N2 O2'
_chemical_formula_sum            'C7 H10 Au Cl N2 O2'
_chemical_formula_weight         386.59

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'
Cl Cl 0.1484 0.1585 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.68619(11)
_cell_length_b                   17.2395(3)
_cell_length_c                   15.2298(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.2421(14)
_cell_angle_gamma                90
_cell_volume                     2016.50(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    109(2)
_cell_measurement_reflns_used    64775
_cell_measurement_theta_min      2.6580
_cell_measurement_theta_max      31.4620

_exptl_crystal_description       irregular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.547
_exptl_crystal_F_000             1424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    14.825
_shelx_estimated_absorpt_T_min   0.249
_shelx_estimated_absorpt_T_max   0.383
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-8 -7 13 0.0716
-10 7 9 0.0666
-1 -22 -8 0.0416
-5 22 -3 0.0399
2 -22 8 0.0428
-3 -23 -5 0.0423
6 10 15 0.0475
-7 -14 -9 0.0544
8 12 10 0.0550
9 -1 -13 0.0817
1 -13 -18 0.0570
11 0 1 0.0678
-7 19 1 0.0485
-9 3 -11 0.0543
0 -20 -12 0.0478
9 -3 11 0.0467
0 24 -2 0.0403
-1 18 -14 0.0507
-4 6 -19 0.0579
-1 -22 9 0.0507
-1 8 -20 0.0583
-4 -19 11 0.0606
5 19 -10 0.0650
-9 -2 12 0.0268
-9 -8 10 0.0207
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-8.3132 -6.7274 13.0497 -0.9917 -0.0781 0.1018
-9.5031 7.1976 8.8498 -0.7588 -0.6480 0.0660
-0.5739 -22.3640 -8.3014 -0.0553 0.7113 0.7007
-4.6394 21.6691 -2.8063 0.0783 -0.9962 -0.0386
2.2801 -21.9211 7.9082 -0.3826 0.9239 -0.0090
-2.5446 -22.7536 -5.4407 -0.2681 0.6490 0.7120
5.7771 10.4373 15.2006 0.0051 -0.0075 -1.0000
-7.4305 -13.7397 -9.2710 -0.3308 0.0804 0.9403
7.9541 11.5540 9.7963 0.3187 0.0241 -0.9476
8.8356 -1.2352 -13.0519 0.9239 0.3826 0.0090
0.7631 -12.9441 -18.1660 0.4503 0.3855 0.8054
10.7869 -0.2328 1.1522 0.6116 0.5215 -0.5950
-6.9747 18.5729 1.4416 -0.2335 -0.9723 -0.0090
-8.8494 2.9251 -11.4205 -0.1413 -0.5848 0.7988
0.1570 -19.7967 -12.4724 0.1508 0.6311 0.7609
8.8886 -3.3262 11.2221 0.1448 0.5996 -0.7871
-0.1351 24.1828 -2.1338 0.3603 -0.8691 -0.3388
-0.6387 17.8846 -14.4157 0.6339 -0.7426 0.2161
-3.9186 5.9806 -18.9884 0.4299 -0.5046 0.7487
-1.3254 -21.6740 9.4418 -0.6447 0.7548 0.1214
-0.6979 7.6767 -20.2528 0.6847 -0.4203 0.5954
-4.3329 -18.5958 11.1543 -0.8409 0.5152 0.1656
4.5775 18.9260 -10.2975 0.8331 -0.5104 -0.2133
-9.2165 -2.3369 11.7989 -0.9524 -0.2822 0.1154
-9.0212 -8.2410 10.0866 -0.9610 -0.0753 0.2660
_exptl_absorpt_correction_T_min  0.68399
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.101a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.700
_oxdiff_exptl_absorpt_empirical_full_max 1.462
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      109(2)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            14688
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.677
_diffrn_reflns_theta_max         31.328
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.900
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.900
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.900
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             14688
_reflns_number_gt                11253
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'CrysAlisPro 1.171.42.101a (Rigaku OD, 2023)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.101a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.101a (Rigaku OD, 2023)'

_computing_structure_solution    
'SHELXT 2018/2 (G. M. Sheldrick, Acta Cryst., 2015, A71, 3-8)'
_computing_structure_refinement  
'SHELXL-2018/3 (G. M. Sheldrick, Acta Cryst., 2015, C71, 3-8)'
_computing_molecular_graphics    ?
_computing_publication_material  
'OLEX2 v1.3 (O. V. Dolomanov et al., J. Appl. Cryst., 2009, 42, 339-341)'

_refine_special_details          
;
 All H atoms were placed in idealised positions and refined using a riding
 model, with a common U restrained to be 1.2 (1.5 for methyl groups) times
 the equivalent isotropic displacement parameter of the parent atom.
 Ordered methyl groups were treated as rigid bodies and allowed to 
 rotate around the E-CH3 bond.

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

 Refined as a 2-component twin. Component 2 rotated by 179.8488° 
 around [0.16 0.77 -0.61] (reciprocal) or [0.58 0.58 -0.58] (direct).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0242P)²+6.3244P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         14688
_refine_ls_number_parameters     242
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0270
_refine_ls_wR_factor_ref         0.0641
_refine_ls_wR_factor_gt          0.0609
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Au1 Au 0.90761(2) 0.66659(2) 0.56680(2) 0.01748(5) Uani 1 1 d . . . . .
Au1A Au 0.64508(2) 0.92065(2) 0.34091(2) 0.02036(5) Uani 1 1 d . . . . .
Cl1 Cl 1.03239(15) 0.72312(7) 0.44910(7) 0.0264(2) Uani 1 1 d . . . . .
Cl1A Cl 0.71096(17) 1.04153(7) 0.29155(8) 0.0306(2) Uani 1 1 d . . . . .
O1 O 0.6271(5) 0.47646(19) 0.9002(2) 0.0257(7) Uani 1 1 d . . . . .
O1A O 0.4180(4) 0.5953(2) 0.5189(2) 0.0237(7) Uani 1 1 d . . . . .
N1 N 0.7814(5) 0.5453(2) 0.6931(2) 0.0185(7) Uani 1 1 d . . . . .
O2A O 0.3989(5) 0.7003(2) 0.6061(2) 0.0269(7) Uani 1 1 d . . . . .
N2 N 0.7313(5) 0.6616(2) 0.7379(2) 0.0168(7) Uani 1 1 d . . . . .
O2 O 0.6562(5) 0.4039(2) 0.7785(3) 0.0327(8) Uani 1 1 d . . . . .
N2A N 0.6244(5) 0.7474(2) 0.3405(2) 0.0201(7) Uani 1 1 d . . . . .
N1A N 0.5139(5) 0.7936(2) 0.4572(2) 0.0201(7) Uani 1 1 d . . . . .
C6 C 0.6607(6) 0.4657(3) 0.8153(3) 0.0218(8) Uani 1 1 d . . . . .
C2 C 0.7033(6) 0.5398(3) 0.7736(3) 0.0187(8) Uani 1 1 d . . . . .
C1A C 0.5903(6) 0.8149(3) 0.3825(3) 0.0206(8) Uani 1 1 d . . . . .
C4 C 0.8419(6) 0.4805(3) 0.6398(3) 0.0242(9) Uani 1 1 d . . . . .
H4A H 0.923736 0.448707 0.675167 0.036 Uiso 1 1 calc R U . . .
H4B H 0.900273 0.500862 0.588587 0.036 Uiso 1 1 calc R U . . .
H4C H 0.742064 0.448785 0.620121 0.036 Uiso 1 1 calc R U . . .
C2A C 0.5010(5) 0.7134(3) 0.4617(3) 0.0179(8) Uani 1 1 d . . . . .
C1 C 0.8008(5) 0.6209(2) 0.6712(3) 0.0170(7) Uani 1 1 d . . . . .
C3A C 0.5707(6) 0.6850(3) 0.3877(3) 0.0197(8) Uani 1 1 d . . . . .
H3A H 0.580381 0.631911 0.371776 0.024 Uiso 1 1 calc R U . . .
C3 C 0.6715(6) 0.6131(2) 0.8009(3) 0.0179(8) Uani 1 1 d . . . . .
H3 H 0.618039 0.627889 0.853566 0.022 Uiso 1 1 calc R U . . .
C6A C 0.4333(6) 0.6714(3) 0.5368(3) 0.0205(8) Uani 1 1 d . . . . .
C4A C 0.4463(7) 0.8490(3) 0.5213(3) 0.0288(10) Uani 1 1 d . . . . .
H4AA H 0.513709 0.844383 0.577002 0.043 Uiso 1 1 calc R U . . .
H4AB H 0.323681 0.837415 0.530871 0.043 Uiso 1 1 calc R U . . .
H4AC H 0.456646 0.901881 0.498562 0.043 Uiso 1 1 calc R U . . .
C5 C 0.7215(6) 0.7466(2) 0.7406(3) 0.0205(8) Uani 1 1 d . . . . .
H5A H 0.811204 0.768625 0.704069 0.031 Uiso 1 1 calc R U . . .
H5B H 0.740412 0.764371 0.801382 0.031 Uiso 1 1 calc R U . . .
H5C H 0.606343 0.763439 0.718303 0.031 Uiso 1 1 calc R U . . .
C7 C 0.5702(7) 0.4076(3) 0.9457(3) 0.0297(10) Uani 1 1 d . . . . .
H7A H 0.460441 0.389081 0.918326 0.045 Uiso 1 1 calc R U . . .
H7B H 0.552742 0.420193 1.007525 0.045 Uiso 1 1 calc R U . . .
H7C H 0.658980 0.367059 0.942140 0.045 Uiso 1 1 calc R U . . .
C5A C 0.7119(6) 0.7425(3) 0.2574(3) 0.0254(9) Uani 1 1 d . . . . .
H5AA H 0.725681 0.794764 0.233197 0.038 Uiso 1 1 calc R U . . .
H5AB H 0.642138 0.710867 0.215805 0.038 Uiso 1 1 calc R U . . .
H5AC H 0.826790 0.718719 0.267321 0.038 Uiso 1 1 calc R U . . .
C7A C 0.3462(7) 0.5497(3) 0.5883(3) 0.0275(10) Uani 1 1 d . . . . .
H7AA H 0.336221 0.495482 0.569555 0.041 Uiso 1 1 calc R U . . .
H7AB H 0.230642 0.569674 0.601437 0.041 Uiso 1 1 calc R U . . .
H7AC H 0.422898 0.553075 0.641130 0.041 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Au1 C1 1.981(4) . ?
Au1 Cl1 2.2841(11) . ?
Au1A C1A 1.981(5) . ?
Au1A Cl1A 2.2789(12) . ?
O1 C6 1.341(6) . ?
O1 C7 1.451(6) . ?
O1A C6A 1.343(6) . ?
O1A C7A 1.444(5) . ?
N1 C1 1.354(6) . ?
N1 C2 1.390(6) . ?
N1 C4 1.466(6) . ?
O2A C6A 1.206(6) . ?
N2 C1 1.362(5) . ?
N2 C3 1.366(5) . ?
N2 C5 1.467(5) . ?
O2 C6 1.203(6) . ?
N2A C1A 1.358(6) . ?
N2A C3A 1.367(6) . ?
N2A C5A 1.459(5) . ?
N1A C1A 1.350(6) . ?
N1A C2A 1.389(6) . ?
N1A C4A 1.474(6) . ?
C6 C2 1.469(6) . ?
C2 C3 1.356(6) . ?
C2A C3A 1.358(6) . ?
C2A C6A 1.466(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
C1 Au1 Cl1 178.05(13) . . ?
C1A Au1A Cl1A 179.13(14) . . ?
C6 O1 C7 114.9(4) . . ?
C6A O1A C7A 114.6(4) . . ?
C1 N1 C2 109.8(4) . . ?
C1 N1 C4 123.8(4) . . ?
C2 N1 C4 126.4(4) . . ?
C1 N2 C3 111.1(4) . . ?
C1 N2 C5 123.9(4) . . ?
C3 N2 C5 124.9(4) . . ?
C1A N2A C3A 111.0(4) . . ?
C1A N2A C5A 124.2(4) . . ?
C3A N2A C5A 124.7(4) . . ?
C1A N1A C2A 110.2(4) . . ?
C1A N1A C4A 123.9(4) . . ?
C2A N1A C4A 125.8(4) . . ?
O2 C6 O1 124.6(4) . . ?
O2 C6 C2 124.9(4) . . ?
O1 C6 C2 110.5(4) . . ?
C3 C2 N1 107.2(4) . . ?
C3 C2 C6 129.3(4) . . ?
N1 C2 C6 123.5(4) . . ?
N1A C1A N2A 105.2(4) . . ?
N1A C1A Au1A 128.6(3) . . ?
N2A C1A Au1A 126.1(3) . . ?
C3A C2A N1A 106.7(4) . . ?
C3A C2A C6A 129.2(4) . . ?
N1A C2A C6A 124.0(4) . . ?
N1 C1 N2 105.2(4) . . ?
N1 C1 Au1 129.3(3) . . ?
N2 C1 Au1 125.5(3) . . ?
C2A C3A N2A 106.8(4) . . ?
C2 C3 N2 106.6(4) . . ?
O2A C6A O1A 124.0(4) . . ?
O2A C6A C2A 125.1(4) . . ?
O1A C6A C2A 110.8(4) . . ?

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
C7 O1 C6 O2 -4.4(7) . . . . ?
C7 O1 C6 C2 175.4(4) . . . . ?
C1 N1 C2 C3 1.1(5) . . . . ?
C4 N1 C2 C3 178.7(4) . . . . ?
C1 N1 C2 C6 178.7(4) . . . . ?
C4 N1 C2 C6 -3.6(7) . . . . ?
O2 C6 C2 C3 161.9(5) . . . . ?
O1 C6 C2 C3 -17.9(7) . . . . ?
O2 C6 C2 N1 -15.2(7) . . . . ?
O1 C6 C2 N1 164.9(4) . . . . ?
C2A N1A C1A N2A 0.1(5) . . . . ?
C4A N1A C1A N2A -176.8(4) . . . . ?
C2A N1A C1A Au1A -179.4(3) . . . . ?
C4A N1A C1A Au1A 3.7(6) . . . . ?
C3A N2A C1A N1A 0.0(5) . . . . ?
C5A N2A C1A N1A -178.2(4) . . . . ?
C3A N2A C1A Au1A 179.6(3) . . . . ?
C5A N2A C1A Au1A 1.4(6) . . . . ?
C1A N1A C2A C3A -0.2(5) . . . . ?
C4A N1A C2A C3A 176.6(4) . . . . ?
C1A N1A C2A C6A 176.4(4) . . . . ?
C4A N1A C2A C6A -6.8(7) . . . . ?
C2 N1 C1 N2 -1.1(5) . . . . ?
C4 N1 C1 N2 -178.8(4) . . . . ?
C2 N1 C1 Au1 178.3(3) . . . . ?
C4 N1 C1 Au1 0.6(6) . . . . ?
C3 N2 C1 N1 0.7(5) . . . . ?
C5 N2 C1 N1 -178.8(4) . . . . ?
C3 N2 C1 Au1 -178.7(3) . . . . ?
C5 N2 C1 Au1 1.8(6) . . . . ?
N1A C2A C3A N2A 0.2(5) . . . . ?
C6A C2A C3A N2A -176.2(4) . . . . ?
C1A N2A C3A C2A -0.1(5) . . . . ?
C5A N2A C3A C2A 178.0(4) . . . . ?
N1 C2 C3 N2 -0.6(5) . . . . ?
C6 C2 C3 N2 -178.1(4) . . . . ?
C1 N2 C3 C2 -0.1(5) . . . . ?
C5 N2 C3 C2 179.4(4) . . . . ?
C7A O1A C6A O2A 3.5(6) . . . . ?
C7A O1A C6A C2A -177.9(4) . . . . ?
C3A C2A C6A O2A 167.5(5) . . . . ?
N1A C2A C6A O2A -8.2(7) . . . . ?
C3A C2A C6A O1A -11.1(7) . . . . ?
N1A C2A C6A O1A 173.1(4) . . . . ?

_refine_diff_density_max         1.941
_refine_diff_density_min         -1.973
_refine_diff_density_rms         0.467

####################################################################### 
# 
# 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_sm40db
_database_code_depnum_ccdc_archive 'CCDC 2355445'
loop_
_audit_author_name
_audit_author_address
'Dirk Bockfeld'
;TU Braunschweig
Germany
;
_audit_update_record             
;
2024-05-14 deposited with the CCDC.	2024-07-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H24 Au Cl2 N4 O4, B F4'
_chemical_formula_sum            'C16 H24 Au B Cl2 F4 N4 O4'
_chemical_formula_weight         691.07

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -4.4197 7.2980 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   10.9098(4)
_cell_length_b                   11.4446(4)
_cell_length_c                   21.1235(4)
_cell_angle_alpha                104.139(2)
_cell_angle_beta                 92.906(2)
_cell_angle_gamma                107.309(3)
_cell_volume                     2419.94(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    51242
_cell_measurement_theta_min      4.3500
_cell_measurement_theta_max      79.9930

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.897
_exptl_crystal_F_000             1336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    14.013
_shelx_estimated_absorpt_T_min   0.213
_shelx_estimated_absorpt_T_max   0.873
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -7 5 0.0493
-7 2 2 0.0739
0 7 -5 0.0960
4 5 -5 0.0848
7 -4 -1 0.0437
1 1 12 0.0036
-1 -1 -12 0.0100
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.5252 -6.8496 5.4349 -0.0112 -0.4705 0.8823
-7.0241 1.6164 2.2836 -0.0246 -0.9481 -0.3172
0.4661 6.8728 -5.4230 0.0110 0.4631 -0.8863
3.8081 4.6953 -5.4459 0.0209 0.8334 -0.5523
6.9225 -3.5903 -0.7422 0.0216 0.8198 0.5722
0.5930 0.7462 12.4694 -0.9996 0.0256 -0.0088
-0.5930 -0.7462 -12.4694 0.9996 -0.0256 0.0088
_exptl_absorpt_correction_T_min  0.182
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.64a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.474
_oxdiff_exptl_absorpt_empirical_full_max 2.081
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            104474
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_av_R_equivalents  0.0775
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         4.176
_diffrn_reflns_theta_max         80.549
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             10403
_reflns_number_gt                9271
_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 1.171.42.64a (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.64a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.64a (Rigaku OD, 2022)'

_computing_structure_solution    
'SHELXT 2018/2 (G. M. Sheldrick, Acta Cryst., 2015, A71, 3-8)'
_computing_structure_refinement  
'SHELXL-2018/3 (G. M. Sheldrick, Acta Cryst., 2015, C71, 3-8)'
_computing_molecular_graphics    ?
_computing_publication_material  
'OLEX2 v1.3 (O. V. Dolomanov et al., J. Appl. Cryst., 2009, 42, 339-341)'

_refine_special_details          
;
 All H atoms were placed in idealised positions and refined using a riding
 model, with a common U restrained to be 1.2 (1.5 for methyl groups) times
 the equivalent isotropic displacement parameter of the parent atom.
 Ordered methyl groups were treated as rigid bodies and allowed to 
 rotate around the E-CH3 bond.

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

 Two BF4 anions were found disordered and refined accordingly. Chemically
 equivalent B-F and F-F distances were restrained to be equal.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0625P)²+2.2371P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.00009(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         10403
_refine_ls_number_parameters     688
_refine_ls_number_restraints     254
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.1200
_refine_ls_wR_factor_gt          0.1176
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_restrained_S_all      1.133
_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 1.000000 1.000000 0.000000 0.02533(8) Uani 1 2 d S . P . .
Cl1 Cl 1.11002(8) 1.20867(8) 0.00942(4) 0.03524(18) Uani 1 1 d . . . . .
O1 O 0.6586(2) 1.2427(2) 0.15323(12) 0.0364(5) Uani 1 1 d . . . . .
O2 O 0.7025(2) 1.1864(3) 0.24501(11) 0.0388(6) Uani 1 1 d . . . . .
N1 N 0.8318(2) 1.1077(3) 0.09200(12) 0.0259(5) Uani 1 1 d . . . . .
N2 N 0.9535(3) 1.0316(3) 0.14294(16) 0.0310(7) Uani 1 1 d . . . . .
C1 C 0.9239(3) 1.0513(3) 0.08429(15) 0.0257(6) Uani 1 1 d . . . . .
C2 C 0.8040(3) 1.1238(3) 0.15650(15) 0.0281(6) Uani 1 1 d . . . . .
C3 C 0.8804(3) 1.0751(3) 0.18764(15) 0.0303(6) Uani 1 1 d . . . . .
H3 H 0.882647 1.071965 0.232201 0.036 Uiso 1 1 calc R U . . .
C4 C 0.7687(3) 1.1408(3) 0.03902(15) 0.0307(7) Uani 1 1 d . . . . .
H4A H 0.675137 1.096817 0.032961 0.046 Uiso 1 1 calc R U . . .
H4B H 0.803646 1.114727 -0.002003 0.046 Uiso 1 1 calc R U . . .
H4C H 0.785014 1.232891 0.050717 0.046 Uiso 1 1 calc R U . . .
C5 C 1.0552(4) 0.9776(4) 0.15764(18) 0.0429(8) Uani 1 1 d . . . . .
H5A H 1.037025 0.892777 0.127370 0.064 Uiso 1 1 calc R U . . .
H5B H 1.056527 0.971321 0.203094 0.064 Uiso 1 1 calc R U . . .
H5C H 1.139538 1.032940 0.152222 0.064 Uiso 1 1 calc R U . . .
C6 C 0.7134(3) 1.1904(3) 0.18283(15) 0.0291(6) Uani 1 1 d . . . . .
C7 C 0.6070(4) 1.2391(4) 0.27580(18) 0.0450(9) Uani 1 1 d . . . . .
H7A H 0.518274 1.180144 0.258756 0.054 Uiso 1 1 calc R U . . .
H7B H 0.614365 1.321581 0.266655 0.054 Uiso 1 1 calc R U . . .
C8 C 0.6356(4) 1.2567(4) 0.34769(18) 0.0510(9) Uani 1 1 d . . . . .
H8A H 0.646899 1.179099 0.355204 0.076 Uiso 1 1 calc R U . . .
H8B H 0.563454 1.274164 0.369688 0.076 Uiso 1 1 calc R U . . .
H8C H 0.715158 1.328265 0.365585 0.076 Uiso 1 1 calc R U . . .
Au1A Au 0.500000 1.000000 0.500000 0.02738(9) Uani 1 2 d S . P . .
Cl1A Cl 0.62171(9) 1.20479(8) 0.50911(4) 0.0430(2) Uani 1 1 d . . . . .
O1A O 0.8307(2) 0.7569(2) 0.34006(11) 0.0335(5) Uani 1 1 d . . . . .
O2A O 0.7488(2) 0.7733(2) 0.24306(10) 0.0343(5) Uani 1 1 d . . . . .
N1A N 0.6635(2) 0.8947(3) 0.40394(12) 0.0266(5) Uani 1 1 d . . . . .
N2A N 0.5071(3) 0.9301(3) 0.35327(14) 0.0333(7) Uani 1 1 d . . . . .
C1A C 0.5634(3) 0.9386(3) 0.41319(15) 0.0282(6) Uani 1 1 d . . . . .
C2A C 0.6710(3) 0.8591(3) 0.33678(14) 0.0283(6) Uani 1 1 d . . . . .
C3A C 0.5733(3) 0.8828(3) 0.30575(15) 0.0328(7) Uani 1 1 d . . . . .
H3A H 0.554295 0.869040 0.259623 0.039 Uiso 1 1 calc R U . . .
C4A C 0.7507(3) 0.8888(4) 0.45719(15) 0.0351(7) Uani 1 1 d . . . . .
H4AA H 0.736024 0.799805 0.456639 0.053 Uiso 1 1 calc R U . . .
H4AB H 0.733660 0.935106 0.499579 0.053 Uiso 1 1 calc R U . . .
H4AC H 0.840711 0.927571 0.451035 0.053 Uiso 1 1 calc R U . . .
C5A C 0.3862(4) 0.9593(4) 0.34079(18) 0.0483(10) Uani 1 1 d . . . . .
H5AA H 0.313647 0.897303 0.352369 0.072 Uiso 1 1 calc R U . . .
H5AB H 0.370027 0.954885 0.294073 0.072 Uiso 1 1 calc R U . . .
H5AC H 0.395028 1.045003 0.367666 0.072 Uiso 1 1 calc R U . . .
C6A C 0.7613(3) 0.7926(3) 0.30861(15) 0.0294(6) Uani 1 1 d . . . . .
C7A C 0.8227(3) 0.6967(3) 0.20795(16) 0.0359(7) Uani 1 1 d . . . . .
H7AA H 0.912481 0.727384 0.230773 0.043 Uiso 1 1 calc R U . . .
H7AB H 0.826418 0.706763 0.162782 0.043 Uiso 1 1 calc R U . . .
C8A C 0.7616(3) 0.5564(3) 0.20432(17) 0.0388(7) Uani 1 1 d . . . . .
H8AA H 0.806601 0.506171 0.175985 0.058 Uiso 1 1 calc R U . . .
H8AB H 0.669949 0.528227 0.186015 0.058 Uiso 1 1 calc R U . . .
H8AC H 0.768825 0.544722 0.248635 0.058 Uiso 1 1 calc R U . . .
Au1B Au 0.500000 0.500000 0.000000 0.02189(8) Uani 1 2 d S . P . .
Cl1B Cl 0.70776(7) 0.50755(8) 0.02742(4) 0.03252(17) Uani 1 1 d . . . . .
O1B O 0.3614(2) 0.5875(2) 0.27130(11) 0.0376(5) Uani 1 1 d . . . . .
O2B O 0.3893(2) 0.4072(2) 0.28543(10) 0.0317(5) Uani 1 1 d . . . . .
N1B N 0.4259(3) 0.5103(3) 0.13710(13) 0.0255(5) Uani 1 1 d . . . . .
N2B N 0.4358(2) 0.3245(2) 0.08876(12) 0.0233(5) Uani 1 1 d . . . . .
C1B C 0.4479(3) 0.4397(3) 0.08075(13) 0.0227(5) Uani 1 1 d . . . . .
C2B C 0.4022(3) 0.4376(3) 0.18190(15) 0.0262(6) Uani 1 1 d . . . . .
C3B C 0.4079(3) 0.3204(3) 0.15070(15) 0.0263(6) Uani 1 1 d . . . . .
H3B H 0.395079 0.249696 0.168534 0.032 Uiso 1 1 calc R U . . .
C4B C 0.4363(3) 0.6449(3) 0.14792(16) 0.0313(6) Uani 1 1 d . . . . .
H4BA H 0.524733 0.698281 0.167471 0.047 Uiso 1 1 calc R U . . .
H4BB H 0.375200 0.665323 0.177780 0.047 Uiso 1 1 calc R U . . .
H4BC H 0.415934 0.660765 0.105715 0.047 Uiso 1 1 calc R U . . .
C5B C 0.4485(3) 0.2172(3) 0.03698(15) 0.0287(6) Uani 1 1 d . . . . .
H5BA H 0.375110 0.187777 0.001921 0.043 Uiso 1 1 calc R U . . .
H5BB H 0.449330 0.147467 0.056032 0.043 Uiso 1 1 calc R U . . .
H5BC H 0.529486 0.245299 0.018653 0.043 Uiso 1 1 calc R U . . .
C6B C 0.3816(3) 0.4880(3) 0.25014(15) 0.0286(6) Uani 1 1 d . . . . .
C7B C 0.3733(3) 0.4472(3) 0.35523(15) 0.0355(7) Uani 1 1 d . . . . .
H7BA H 0.346045 0.371666 0.372476 0.043 Uiso 1 1 calc R U . . .
H7BB H 0.304760 0.487985 0.359671 0.043 Uiso 1 1 calc R U . . .
C8B C 0.4978(4) 0.5390(4) 0.39470(19) 0.0447(9) Uani 1 1 d . . . . .
H8BA H 0.521149 0.616630 0.379940 0.067 Uiso 1 1 calc R U . . .
H8BB H 0.566720 0.500103 0.388472 0.067 Uiso 1 1 calc R U . . .
H8BC H 0.486964 0.560169 0.441455 0.067 Uiso 1 1 calc R U . . .
Au1C Au 0.000000 0.500000 0.500000 0.02746(9) Uani 1 2 d S . P . .
Cl1C Cl 0.20157(8) 0.47810(8) 0.50617(4) 0.03759(18) Uani 1 1 d . . . . .
O1C O 0.0670(3) 0.3633(2) 0.21753(13) 0.0470(6) Uani 1 1 d . . . . .
O2C O 0.0652(2) 0.5504(2) 0.20175(11) 0.0356(5) Uani 1 1 d . . . . .
N1C N 0.0307(3) 0.4623(3) 0.35495(16) 0.0305(7) Uani 1 1 d . . . . .
N2C N 0.0420(3) 0.6563(2) 0.40150(13) 0.0292(5) Uani 1 1 d . . . . .
C1C C 0.0258(3) 0.5418(3) 0.41237(15) 0.0290(6) Uani 1 1 d . . . . .
C2C C 0.0503(3) 0.5281(3) 0.30687(16) 0.0305(6) Uani 1 1 d . . . . .
C3C C 0.0573(3) 0.6498(3) 0.33734(16) 0.0306(6) Uani 1 1 d . . . . .
H3C H 0.070438 0.717768 0.317429 0.037 Uiso 1 1 calc R U . . .
C4C C 0.0122(4) 0.3257(3) 0.34535(17) 0.0369(7) Uani 1 1 d . . . . .
H4CA H -0.067774 0.275207 0.315405 0.055 Uiso 1 1 calc R U . . .
H4CB H 0.006079 0.305868 0.387893 0.055 Uiso 1 1 calc R U . . .
H4CC H 0.085908 0.305380 0.326378 0.055 Uiso 1 1 calc R U . . .
C5C C 0.0426(4) 0.7708(3) 0.45217(17) 0.0359(7) Uani 1 1 d . . . . .
H5CA H -0.038997 0.753570 0.471050 0.054 Uiso 1 1 calc R U . . .
H5CB H 0.052010 0.841215 0.432125 0.054 Uiso 1 1 calc R U . . .
H5CC H 0.115195 0.793904 0.487026 0.054 Uiso 1 1 calc R U . . .
C6C C 0.0621(3) 0.4699(3) 0.23839(17) 0.0345(7) Uani 1 1 d . . . . .
C7C C 0.0722(4) 0.5005(4) 0.13178(18) 0.0440(8) Uani 1 1 d . . . . .
H7CA H -0.001218 0.421603 0.112482 0.053 Uiso 1 1 calc R U . . .
H7CB H 0.153995 0.480738 0.126094 0.053 Uiso 1 1 calc R U . . .
C8C C 0.0665(4) 0.6003(4) 0.09843(19) 0.0487(9) Uani 1 1 d . . . . .
H8CA H 0.081201 0.573848 0.052488 0.073 Uiso 1 1 calc R U . . .
H8CB H 0.133499 0.680784 0.121166 0.073 Uiso 1 1 calc R U . . .
H8CC H -0.018928 0.611820 0.099778 0.073 Uiso 1 1 calc R U . . .
F1A F 0.3197(4) 0.8186(4) 0.0863(2) 0.0603(12) Uani 0.851(6) 1 d D . P A 1
F2A F 0.5126(3) 0.9625(3) 0.08792(18) 0.0662(11) Uani 0.851(6) 1 d D . P A 1
F3A F 0.4513(5) 0.9232(3) 0.18261(14) 0.0689(13) Uani 0.851(6) 1 d D . P A 1
F4A F 0.3525(5) 1.0286(4) 0.1312(2) 0.0437(11) Uani 0.851(6) 1 d D . P A 1
B1A B 0.4097(5) 0.9339(5) 0.1226(3) 0.0333(11) Uani 0.851(6) 1 d D . P A 1
F1B F 0.3532(17) 0.834(2) 0.0787(7) 0.031(4) Uani 0.149(6) 1 d D U P A 2
F2B F 0.5192(13) 0.946(2) 0.1592(11) 0.083(8) Uani 0.149(6) 1 d D . P A 2
F3B F 0.369(3) 1.0342(19) 0.1370(15) 0.069(10) Uani 0.149(6) 1 d D . P A 2
F4B F 0.3167(16) 0.8725(14) 0.1839(6) 0.054(5) Uani 0.149(6) 1 d D . P A 2
B1B B 0.3896(17) 0.9225(17) 0.1395(8) 0.034(5) Uani 0.149(6) 1 d D . P A 2
F1C F 0.9651(9) 1.0469(12) 0.3274(7) 0.037(2) Uani 0.56(4) 1 d D . P B 3
F2C F 1.1814(11) 1.1401(12) 0.3417(12) 0.068(4) Uani 0.56(4) 1 d D . P B 3
F3C F 1.0979(14) 0.9276(12) 0.3184(7) 0.050(2) Uani 0.56(4) 1 d D . P B 3
F4C F 1.085(3) 1.0490(14) 0.4171(6) 0.083(4) Uani 0.56(4) 1 d D . P B 3
B1C B 1.0827(12) 1.0419(13) 0.3510(8) 0.039(3) Uani 0.56(4) 1 d D . P B 3
F1D F 1.0485(18) 1.056(2) 0.4245(7) 0.065(4) Uani 0.44(4) 1 d D . P B 4
F2D F 1.1905(19) 1.1464(19) 0.3639(15) 0.084(6) Uani 0.44(4) 1 d D . P B 4
F3D F 1.109(2) 0.9334(16) 0.3408(16) 0.071(5) Uani 0.44(4) 1 d D . P B 4
F4D F 0.982(2) 1.046(2) 0.3208(10) 0.070(5) Uani 0.44(4) 1 d D . P B 4
B1D B 1.0826(17) 1.0466(15) 0.3622(9) 0.032(4) Uani 0.44(4) 1 d D . P B 4


_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 2.033(3) 2_775 ?
Au1 C1 2.033(3) . ?
Au1 Cl1 2.2851(8) . ?
Au1 Cl1 2.2851(8) 2_775 ?
O1 C6 1.211(4) . ?
O2 C6 1.336(4) . ?
O2 C7 1.457(4) . ?
N1 C1 1.343(4) . ?
N1 C2 1.391(4) . ?
N1 C4 1.468(4) . ?
N2 C1 1.352(4) . ?
N2 C3 1.363(4) . ?
N2 C5 1.475(4) . ?
C2 C3 1.356(4) . ?
C2 C6 1.471(4) . ?
C7 C8 1.486(5) . ?
Au1A C1A 2.031(3) 2_676 ?
Au1A C1A 2.031(3) . ?
Au1A Cl1A 2.2792(9) 2_676 ?
Au1A Cl1A 2.2793(9) . ?
O1A C6A 1.204(4) . ?
O2A C6A 1.341(4) . ?
O2A C7A 1.460(4) . ?
N1A C1A 1.336(4) . ?
N1A C2A 1.391(4) . ?
N1A C4A 1.463(4) . ?
N2A C1A 1.347(4) . ?
N2A C3A 1.365(4) . ?
N2A C5A 1.480(4) . ?
C2A C3A 1.352(4) . ?
C2A C6A 1.479(4) . ?
C7A C8A 1.525(5) . ?
Au1B C1B 2.037(3) 2_665 ?
Au1B C1B 2.037(3) . ?
Au1B Cl1B 2.2817(7) . ?
Au1B Cl1B 2.2818(7) 2_665 ?
O1B C6B 1.207(4) . ?
O2B C6B 1.339(4) . ?
O2B C7B 1.469(4) . ?
N1B C1B 1.342(4) . ?
N1B C2B 1.391(4) . ?
N1B C4B 1.469(4) . ?
N2B C1B 1.339(4) . ?
N2B C3B 1.367(4) . ?
N2B C5B 1.478(4) . ?
C2B C3B 1.364(4) . ?
C2B C6B 1.471(4) . ?
C7B C8B 1.501(5) . ?
Au1C C1C 2.034(3) . ?
Au1C C1C 2.035(3) 2_566 ?
Au1C Cl1C 2.2870(8) 2_566 ?
Au1C Cl1C 2.2871(8) . ?
O1C C6C 1.209(4) . ?
O2C C6C 1.335(4) . ?
O2C C7C 1.463(4) . ?
N1C C1C 1.341(4) . ?
N1C C2C 1.394(5) . ?
N1C C4C 1.476(4) . ?
N2C C1C 1.347(4) . ?
N2C C3C 1.361(4) . ?
N2C C5C 1.474(4) . ?
C2C C3C 1.362(4) . ?
C2C C6C 1.467(5) . ?
C7C C8C 1.495(6) . ?
F1A B1A 1.396(6) . ?
F2A B1A 1.373(6) . ?
F3A B1A 1.372(5) . ?
F4A B1A 1.384(5) . ?
F1B B1B 1.379(13) . ?
F2B B1B 1.380(13) . ?
F3B B1B 1.375(13) . ?
F4B B1B 1.382(13) . ?
F1C B1C 1.375(9) . ?
F2C B1C 1.367(9) . ?
F3C B1C 1.383(10) . ?
F4C B1C 1.377(10) . ?
F1D B1D 1.373(12) . ?
F2D B1D 1.366(11) . ?
F3D B1D 1.385(11) . ?
F4D B1D 1.368(12) . ?

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 C1 180.0 2_775 . ?
C1 Au1 Cl1 89.66(9) 2_775 . ?
C1 Au1 Cl1 90.34(9) . . ?
C1 Au1 Cl1 90.34(9) 2_775 2_775 ?
C1 Au1 Cl1 89.66(9) . 2_775 ?
Cl1 Au1 Cl1 180.0 . 2_775 ?
C6 O2 C7 115.7(3) . . ?
C1 N1 C2 109.0(3) . . ?
C1 N1 C4 124.3(2) . . ?
C2 N1 C4 126.7(2) . . ?
C1 N2 C3 110.1(3) . . ?
C1 N2 C5 125.0(3) . . ?
C3 N2 C5 124.7(3) . . ?
N1 C1 N2 106.8(3) . . ?
N1 C1 Au1 126.7(2) . . ?
N2 C1 Au1 126.5(2) . . ?
C3 C2 N1 107.1(3) . . ?
C3 C2 C6 129.7(3) . . ?
N1 C2 C6 123.2(3) . . ?
C2 C3 N2 107.0(3) . . ?
O1 C6 O2 125.0(3) . . ?
O1 C6 C2 125.4(3) . . ?
O2 C6 C2 109.6(3) . . ?
O2 C7 C8 106.2(3) . . ?
C1A Au1A C1A 180.0 2_676 . ?
C1A Au1A Cl1A 91.09(10) 2_676 2_676 ?
C1A Au1A Cl1A 88.91(10) . 2_676 ?
C1A Au1A Cl1A 88.91(10) 2_676 . ?
C1A Au1A Cl1A 91.09(10) . . ?
Cl1A Au1A Cl1A 180.0 2_676 . ?
C6A O2A C7A 115.5(2) . . ?
C1A N1A C2A 108.9(3) . . ?
C1A N1A C4A 124.2(3) . . ?
C2A N1A C4A 126.9(3) . . ?
C1A N2A C3A 109.9(3) . . ?
C1A N2A C5A 124.8(3) . . ?
C3A N2A C5A 125.2(3) . . ?
N1A C1A N2A 107.1(3) . . ?
N1A C1A Au1A 127.4(2) . . ?
N2A C1A Au1A 125.4(2) . . ?
C3A C2A N1A 107.0(3) . . ?
C3A C2A C6A 129.4(3) . . ?
N1A C2A C6A 123.1(3) . . ?
C2A C3A N2A 107.0(3) . . ?
O1A C6A O2A 125.8(3) . . ?
O1A C6A C2A 124.5(3) . . ?
O2A C6A C2A 109.7(3) . . ?
O2A C7A C8A 111.3(3) . . ?
C1B Au1B C1B 180.0 2_665 . ?
C1B Au1B Cl1B 90.04(8) 2_665 . ?
C1B Au1B Cl1B 89.96(8) . . ?
C1B Au1B Cl1B 89.97(8) 2_665 2_665 ?
C1B Au1B Cl1B 90.04(8) . 2_665 ?
Cl1B Au1B Cl1B 180.0 . 2_665 ?
C6B O2B C7B 115.7(2) . . ?
C1B N1B C2B 108.8(3) . . ?
C1B N1B C4B 123.0(3) . . ?
C2B N1B C4B 128.1(3) . . ?
C1B N2B C3B 110.4(2) . . ?
C1B N2B C5B 124.2(2) . . ?
C3B N2B C5B 125.4(3) . . ?
N2B C1B N1B 107.3(2) . . ?
N2B C1B Au1B 126.4(2) . . ?
N1B C1B Au1B 126.3(2) . . ?
C3B C2B N1B 107.0(3) . . ?
C3B C2B C6B 129.8(3) . . ?
N1B C2B C6B 123.2(3) . . ?
C2B C3B N2B 106.6(3) . . ?
O1B C6B O2B 125.0(3) . . ?
O1B C6B C2B 125.1(3) . . ?
O2B C6B C2B 109.9(2) . . ?
O2B C7B C8B 110.7(3) . . ?
C1C Au1C C1C 180.0 . 2_566 ?
C1C Au1C Cl1C 90.53(9) . 2_566 ?
C1C Au1C Cl1C 89.47(9) 2_566 2_566 ?
C1C Au1C Cl1C 89.47(9) . . ?
C1C Au1C Cl1C 90.53(9) 2_566 . ?
Cl1C Au1C Cl1C 180.00(4) 2_566 . ?
C6C O2C C7C 115.3(3) . . ?
C1C N1C C2C 109.3(3) . . ?
C1C N1C C4C 124.0(3) . . ?
C2C N1C C4C 126.7(3) . . ?
C1C N2C C3C 110.0(3) . . ?
C1C N2C C5C 124.5(3) . . ?
C3C N2C C5C 125.6(3) . . ?
N1C C1C N2C 107.0(3) . . ?
N1C C1C Au1C 127.1(2) . . ?
N2C C1C Au1C 125.9(2) . . ?
C3C C2C N1C 106.2(3) . . ?
C3C C2C C6C 130.2(3) . . ?
N1C C2C C6C 123.6(3) . . ?
N2C C3C C2C 107.5(3) . . ?
O1C C6C O2C 124.4(3) . . ?
O1C C6C C2C 125.0(3) . . ?
O2C C6C C2C 110.6(3) . . ?
O2C C7C C8C 107.6(3) . . ?
F3A B1A F2A 109.9(4) . . ?
F3A B1A F4A 110.0(4) . . ?
F2A B1A F4A 109.5(4) . . ?
F3A B1A F1A 109.7(4) . . ?
F2A B1A F1A 108.4(4) . . ?
F4A B1A F1A 109.3(4) . . ?
F3B B1B F1B 111.0(12) . . ?
F3B B1B F2B 109.6(12) . . ?
F1B B1B F2B 109.1(12) . . ?
F3B B1B F4B 109.3(12) . . ?
F1B B1B F4B 108.3(11) . . ?
F2B B1B F4B 109.5(12) . . ?
F2C B1C F1C 110.4(8) . . ?
F2C B1C F4C 110.0(9) . . ?
F1C B1C F4C 109.0(8) . . ?
F2C B1C F3C 109.4(8) . . ?
F1C B1C F3C 109.6(9) . . ?
F4C B1C F3C 108.5(9) . . ?
F2D B1D F4D 110.6(11) . . ?
F2D B1D F1D 109.4(11) . . ?
F4D B1D F1D 109.4(10) . . ?
F2D B1D F3D 109.6(11) . . ?
F4D B1D F3D 109.6(11) . . ?
F1D B1D F3D 108.2(10) . . ?

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
C2 N1 C1 N2 0.2(4) . . . . ?
C4 N1 C1 N2 -177.3(3) . . . . ?
C2 N1 C1 Au1 178.4(2) . . . . ?
C4 N1 C1 Au1 0.8(5) . . . . ?
C3 N2 C1 N1 0.1(4) . . . . ?
C5 N2 C1 N1 -176.6(3) . . . . ?
C3 N2 C1 Au1 -178.1(2) . . . . ?
C5 N2 C1 Au1 5.2(5) . . . . ?
C1 N1 C2 C3 -0.4(4) . . . . ?
C4 N1 C2 C3 177.1(3) . . . . ?
C1 N1 C2 C6 175.8(3) . . . . ?
C4 N1 C2 C6 -6.7(5) . . . . ?
N1 C2 C3 N2 0.4(4) . . . . ?
C6 C2 C3 N2 -175.4(3) . . . . ?
C1 N2 C3 C2 -0.3(4) . . . . ?
C5 N2 C3 C2 176.4(3) . . . . ?
C7 O2 C6 O1 6.1(5) . . . . ?
C7 O2 C6 C2 -174.9(3) . . . . ?
C3 C2 C6 O1 171.8(4) . . . . ?
N1 C2 C6 O1 -3.5(5) . . . . ?
C3 C2 C6 O2 -7.2(5) . . . . ?
N1 C2 C6 O2 177.5(3) . . . . ?
C6 O2 C7 C8 -165.2(3) . . . . ?
C2A N1A C1A N2A 0.6(4) . . . . ?
C4A N1A C1A N2A 179.5(3) . . . . ?
C2A N1A C1A Au1A 178.2(2) . . . . ?
C4A N1A C1A Au1A -2.9(5) . . . . ?
C3A N2A C1A N1A -1.1(4) . . . . ?
C5A N2A C1A N1A 174.9(4) . . . . ?
C3A N2A C1A Au1A -178.7(3) . . . . ?
C5A N2A C1A Au1A -2.7(5) . . . . ?
C1A N1A C2A C3A 0.1(4) . . . . ?
C4A N1A C2A C3A -178.8(3) . . . . ?
C1A N1A C2A C6A -172.6(3) . . . . ?
C4A N1A C2A C6A 8.5(5) . . . . ?
N1A C2A C3A N2A -0.8(4) . . . . ?
C6A C2A C3A N2A 171.3(3) . . . . ?
C1A N2A C3A C2A 1.2(4) . . . . ?
C5A N2A C3A C2A -174.8(4) . . . . ?
C7A O2A C6A O1A 3.1(5) . . . . ?
C7A O2A C6A C2A -173.9(3) . . . . ?
C3A C2A C6A O1A -166.7(4) . . . . ?
N1A C2A C6A O1A 4.4(5) . . . . ?
C3A C2A C6A O2A 10.4(5) . . . . ?
N1A C2A C6A O2A -178.6(3) . . . . ?
C6A O2A C7A C8A 74.1(4) . . . . ?
C3B N2B C1B N1B -1.0(3) . . . . ?
C5B N2B C1B N1B 177.9(3) . . . . ?
C3B N2B C1B Au1B 175.9(2) . . . . ?
C5B N2B C1B Au1B -5.1(4) . . . . ?
C2B N1B C1B N2B 1.4(3) . . . . ?
C4B N1B C1B N2B 177.2(3) . . . . ?
C2B N1B C1B Au1B -175.6(2) . . . . ?
C4B N1B C1B Au1B 0.3(4) . . . . ?
C1B N1B C2B C3B -1.2(3) . . . . ?
C4B N1B C2B C3B -176.8(3) . . . . ?
C1B N1B C2B C6B 176.4(3) . . . . ?
C4B N1B C2B C6B 0.8(5) . . . . ?
N1B C2B C3B N2B 0.6(3) . . . . ?
C6B C2B C3B N2B -176.8(3) . . . . ?
C1B N2B C3B C2B 0.3(3) . . . . ?
C5B N2B C3B C2B -178.6(3) . . . . ?
C7B O2B C6B O1B -1.0(5) . . . . ?
C7B O2B C6B C2B 178.7(3) . . . . ?
C3B C2B C6B O1B -170.0(3) . . . . ?
N1B C2B C6B O1B 13.0(5) . . . . ?
C3B C2B C6B O2B 10.4(5) . . . . ?
N1B C2B C6B O2B -166.6(3) . . . . ?
C6B O2B C7B C8B -81.4(3) . . . . ?
C2C N1C C1C N2C 0.0(4) . . . . ?
C4C N1C C1C N2C -177.6(3) . . . . ?
C2C N1C C1C Au1C -179.7(2) . . . . ?
C4C N1C C1C Au1C 2.7(5) . . . . ?
C3C N2C C1C N1C -0.1(4) . . . . ?
C5C N2C C1C N1C 179.8(3) . . . . ?
C3C N2C C1C Au1C 179.6(2) . . . . ?
C5C N2C C1C Au1C -0.5(4) . . . . ?
C1C N1C C2C C3C 0.1(4) . . . . ?
C4C N1C C2C C3C 177.6(3) . . . . ?
C1C N1C C2C C6C 179.2(3) . . . . ?
C4C N1C C2C C6C -3.3(5) . . . . ?
C1C N2C C3C C2C 0.1(4) . . . . ?
C5C N2C C3C C2C -179.8(3) . . . . ?
N1C C2C C3C N2C -0.1(4) . . . . ?
C6C C2C C3C N2C -179.1(3) . . . . ?
C7C O2C C6C O1C 1.3(5) . . . . ?
C7C O2C C6C C2C -177.9(3) . . . . ?
C3C C2C C6C O1C 172.4(3) . . . . ?
N1C C2C C6C O1C -6.4(5) . . . . ?
C3C C2C C6C O2C -8.4(5) . . . . ?
N1C C2C C6C O2C 172.8(3) . . . . ?
C6C O2C C7C C8C 176.6(3) . . . . ?

_refine_diff_density_max         1.360
_refine_diff_density_min         -1.754
_refine_diff_density_rms         0.150

####################################################################### 
# 
# 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_sm31db
_database_code_depnum_ccdc_archive 'CCDC 2355442'
loop_
_audit_author_name
_audit_author_address
'Dirk Bockfeld'
;TU Braunschweig
Germany
;
_audit_update_record             
;
2024-05-14 deposited with the CCDC.	2024-07-30 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT971_sm31db              
;
PROBLEM: Check Calcd Resid. Dens.
RESPONSE: The residual density can be attributed to absorption effects.
 Additionally, the dataset was recorded to a high diffraction angle.
 Usually larger residual electron density is observed in these cases.
;
_vrf_PLAT972_sm31db              
;
PROBLEM: Check Calcd Resid. Dens.
RESPONSE: The residual density can be attributed to absorption effects.
 Additionally, the dataset was recorded to a high diffraction angle.
 Usually larger residual electron density is observed in these cases.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H10 Au Cl3 N2 O2, C H Cl3'
_chemical_formula_sum            'C8 H11 Au Cl6 N2 O2'
_chemical_formula_weight         576.85

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'
Cl Cl 0.1484 0.1585 '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'

_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                   7.9945(2)
_cell_length_b                   10.9103(2)
_cell_length_c                   19.0105(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.267(2)
_cell_angle_gamma                90
_cell_volume                     1631.59(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    68278
_cell_measurement_theta_min      2.5840
_cell_measurement_theta_max      66.9320

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.348
_exptl_crystal_F_000             1080
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    9.995
_shelx_estimated_absorpt_T_min   0.142
_shelx_estimated_absorpt_T_max   0.585
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 14 8 0.1175
-1 0 27 0.0133
1 0 -27 0.0542
-2 -15 0 0.1725
11 -1 -3 0.0345
-11 1 3 0.0278
4 -14 0 0.1559
-3 15 0 0.1334
-9 0 -13 0.0374
9 -1 14 0.0229
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.4903 14.4492 7.6850 0.0277 -0.3380 0.9407
-1.0460 -0.3774 26.6955 0.0781 -0.9950 -0.0623
0.9447 -0.4379 -26.6689 -0.0783 0.9969 0.0085
-1.8511 -15.1583 -0.3792 -0.0066 0.0678 -0.9977
11.2207 -0.5990 -2.5445 0.9887 0.0776 0.1286
-11.2203 0.6135 2.5435 -0.9888 -0.0776 -0.1276
3.9335 -14.3877 0.0134 0.5023 0.0405 -0.8637
-3.4225 14.6320 -0.1466 -0.4603 -0.0372 0.8870
-8.5736 -0.0585 -13.4776 -0.8465 0.5190 -0.1182
8.5257 -0.6184 13.5985 0.8502 -0.5212 0.0740
_exptl_absorpt_correction_T_min  0.263
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.64a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.795
_oxdiff_exptl_absorpt_empirical_full_max 1.488
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            289263
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_av_R_equivalents  0.0626
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -48
_diffrn_reflns_limit_l_max       48
_diffrn_reflns_theta_min         2.161
_diffrn_reflns_theta_max         65.671
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             28759
_reflns_number_gt                20198
_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 1.171.42.64a (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.64a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.64a (Rigaku OD, 2022)'

_computing_structure_solution    
'SHELXT 2018/2 (G. M. Sheldrick, Acta Cryst., 2015, A71, 3-8)'
_computing_structure_refinement  
'SHELXL-2018/3 (G. M. Sheldrick, Acta Cryst., 2015, C71, 3-8)'
_computing_molecular_graphics    ?
_computing_publication_material  
'OLEX2 v1.3 (O. V. Dolomanov et al., J. Appl. Cryst., 2009, 42, 339-341)'

_refine_special_details          
;
 All H atoms were placed in idealised positions and refined using a riding
 model, with a common U restrained to be 1.2 (1.5 for methyl groups) times
 the equivalent isotropic displacement parameter of the parent atom.
 Ordered methyl groups were treated as rigid bodies and allowed to 
 rotate around the E-CH3 bond.

 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0337P)²+1.9499P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         28759
_refine_ls_number_parameters     175
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_ref         0.0842
_refine_ls_wR_factor_gt          0.0750
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.006
_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 -0.02424(2) 0.79507(2) 0.59474(2) 0.01218(1) Uani 1 1 d . . . . .
Cl1 Cl -0.30427(5) 0.77372(4) 0.53876(2) 0.01761(5) Uani 1 1 d . . . . .
Cl2 Cl -0.07874(6) 0.98381(4) 0.63769(3) 0.02275(7) Uani 1 1 d . . . . .
Cl3 Cl 0.04082(5) 0.60904(4) 0.55385(3) 0.02382(7) Uani 1 1 d . . . . .
O1 O 0.72412(16) 0.81470(13) 0.78996(8) 0.0204(2) Uani 1 1 d . . . . .
O2 O 0.5598(2) 0.66199(16) 0.81946(9) 0.0295(3) Uani 1 1 d . . . . .
N1 N 0.33593(15) 0.88481(12) 0.62223(7) 0.01487(15) Uani 1 1 d . . . . .
N2 N 0.29399(16) 0.75072(11) 0.70148(7) 0.01468(15) Uani 1 1 d . . . . .
C1 C 0.21904(17) 0.81020(12) 0.64269(8) 0.01394(17) Uani 1 1 d . . . . .
C2 C 0.48653(17) 0.87383(14) 0.66908(8) 0.01519(18) Uani 1 1 d . . . . .
H2 H 0.588968 0.916688 0.666989 0.018 Uiso 1 1 calc R U . . .
C3 C 0.46173(18) 0.78982(13) 0.71925(8) 0.01483(17) Uani 1 1 d . . . . .
C4 C 0.3091(2) 0.96370(17) 0.55902(9) 0.0202(2) Uani 1 1 d . . . . .
H4A H 0.335518 0.917983 0.518003 0.030 Uiso 1 1 calc R U . . .
H4B H 0.383463 1.035510 0.567895 0.030 Uiso 1 1 calc R U . . .
H4C H 0.190176 0.990462 0.548813 0.030 Uiso 1 1 calc R U . . .
C5 C 0.2111(2) 0.65842(18) 0.73948(10) 0.0220(3) Uani 1 1 d . . . . .
H5A H 0.089821 0.654575 0.718758 0.033 Uiso 1 1 calc R U . . .
H5B H 0.224570 0.680723 0.790113 0.033 Uiso 1 1 calc R U . . .
H5C H 0.263344 0.578216 0.734984 0.033 Uiso 1 1 calc R U . . .
C6 C 0.58386(19) 0.74664(15) 0.78158(9) 0.0175(2) Uani 1 1 d . . . . .
C7 C 0.8498(2) 0.78740(19) 0.85300(12) 0.0257(3) Uani 1 1 d . . . . .
H7A H 0.946114 0.843728 0.855460 0.039 Uiso 1 1 calc R U . . .
H7B H 0.889501 0.702850 0.850307 0.039 Uiso 1 1 calc R U . . .
H7C H 0.798518 0.797192 0.895809 0.039 Uiso 1 1 calc R U . . .
Cl4 Cl 0.44623(6) 0.51704(5) 0.59553(3) 0.02730(8) Uani 1 1 d . . . . .
Cl5 Cl 0.68480(9) 0.32024(6) 0.58222(4) 0.03496(11) Uani 1 1 d . . . . .
Cl6 Cl 0.77260(7) 0.50392(6) 0.69162(3) 0.02864(9) Uani 1 1 d . . . . .
C8 C 0.6618(2) 0.47534(17) 0.60375(10) 0.0214(3) Uani 1 1 d . . . . .
H8 H 0.714118 0.526509 0.569782 0.026 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Au1 C1 2.0022(14) . ?
Au1 Cl3 2.2668(4) . ?
Au1 Cl2 2.2855(4) . ?
Au1 Cl1 2.3129(4) . ?
O1 C6 1.331(2) . ?
O1 C7 1.451(2) . ?
O2 C6 1.207(2) . ?
N1 C1 1.3478(18) . ?
N1 C2 1.3692(19) . ?
N1 C4 1.463(2) . ?
N2 C1 1.3381(19) . ?
N2 C3 1.3903(18) . ?
N2 C5 1.465(2) . ?
C2 C3 1.363(2) . ?
C3 C6 1.472(2) . ?
Cl4 C8 1.7620(18) . ?
Cl5 C8 1.758(2) . ?
Cl6 C8 1.774(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
C1 Au1 Cl3 88.07(4) . . ?
C1 Au1 Cl2 89.70(4) . . ?
Cl3 Au1 Cl2 177.747(15) . . ?
C1 Au1 Cl1 178.89(4) . . ?
Cl3 Au1 Cl1 90.829(15) . . ?
Cl2 Au1 Cl1 91.410(15) . . ?
C6 O1 C7 115.40(15) . . ?
C1 N1 C2 109.51(12) . . ?
C1 N1 C4 125.78(13) . . ?
C2 N1 C4 124.70(12) . . ?
C1 N2 C3 108.84(12) . . ?
C1 N2 C5 124.79(13) . . ?
C3 N2 C5 126.36(13) . . ?
N2 C1 N1 107.68(12) . . ?
N2 C1 Au1 126.46(10) . . ?
N1 C1 Au1 125.84(10) . . ?
C3 C2 N1 107.06(12) . . ?
C2 C3 N2 106.91(12) . . ?
C2 C3 C6 128.35(13) . . ?
N2 C3 C6 124.75(13) . . ?
O2 C6 O1 125.16(15) . . ?
O2 C6 C3 124.87(15) . . ?
O1 C6 C3 109.97(13) . . ?
Cl5 C8 Cl4 111.67(10) . . ?
Cl5 C8 Cl6 109.45(10) . . ?
Cl4 C8 Cl6 110.77(11) . . ?

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
C3 N2 C1 N1 0.82(17) . . . . ?
C5 N2 C1 N1 -178.35(15) . . . . ?
C3 N2 C1 Au1 -177.74(10) . . . . ?
C5 N2 C1 Au1 3.1(2) . . . . ?
C2 N1 C1 N2 -0.76(17) . . . . ?
C4 N1 C1 N2 177.95(15) . . . . ?
C2 N1 C1 Au1 177.82(10) . . . . ?
C4 N1 C1 Au1 -3.5(2) . . . . ?
C1 N1 C2 C3 0.39(17) . . . . ?
C4 N1 C2 C3 -178.33(15) . . . . ?
N1 C2 C3 N2 0.11(17) . . . . ?
N1 C2 C3 C6 -179.28(15) . . . . ?
C1 N2 C3 C2 -0.58(17) . . . . ?
C5 N2 C3 C2 178.58(16) . . . . ?
C1 N2 C3 C6 178.84(14) . . . . ?
C5 N2 C3 C6 -2.0(3) . . . . ?
C7 O1 C6 O2 -4.4(3) . . . . ?
C7 O1 C6 C3 175.48(16) . . . . ?
C2 C3 C6 O2 -171.2(2) . . . . ?
N2 C3 C6 O2 9.5(3) . . . . ?
C2 C3 C6 O1 8.9(2) . . . . ?
N2 C3 C6 O1 -170.38(15) . . . . ?

_refine_diff_density_max         2.527
_refine_diff_density_min         -4.379
_refine_diff_density_rms         0.234

