# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_kby-499_4_twin1_hklf4
_database_code_depnum_ccdc_archive 'CCDC 1858874'
_audit_update_record             
;
2018-07-28 deposited with the CCDC.
2018-09-12 downloaded from the CCDC.
;
_audit_creation_date             2018-03-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        1B
_chemical_formula_moiety         'C14 H5 Au F5 N O2'
_chemical_formula_sum            'C14 H5 Au F5 N O2'
_chemical_formula_weight         511.16
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C13 H12 F10 Au'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.3857(3)
_cell_length_b                   7.4524(3)
_cell_length_c                   27.7545(9)
_cell_angle_alpha                82.335(3)
_cell_angle_beta                 89.173(3)
_cell_angle_gamma                60.856(4)
_cell_volume                     1320.06(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    15712
_cell_measurement_temperature    123
_cell_measurement_theta_max      29.1220
_cell_measurement_theta_min      2.9780
_shelx_estimated_absorpt_T_max   0.394
_shelx_estimated_absorpt_T_min   0.068
_exptl_absorpt_coefficient_mu    11.213
_exptl_absorpt_correction_T_max  0.08089
_exptl_absorpt_correction_T_min  0.05466
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.45g (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.572
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.521
_exptl_crystal_size_mid          0.152
_exptl_crystal_size_min          0.102
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0063
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.902
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            11383
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.902
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.140
_diffrn_reflns_theta_min         2.225
_diffrn_ambient_temperature      123
_diffrn_detector                 'PLATUS 200K area detector'
_diffrn_detector_area_resol_mean 5.811
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.902
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -97.00 -34.00   0.50    6.19    --   -7.30  60.00  60.00  126
  2  ω     38.00  64.00   0.50    6.19    --   -7.30  60.00  60.00   52
  3  ω    -20.00   6.00   0.50    6.19    --   -7.30  60.00 120.00   52
  4  ω     10.00  82.00   0.50    6.19    --   -7.30  60.00 120.00  144
  5  ω    -86.00 -60.00   0.50    6.19    --   -7.30  43.00  90.00   52
  6  ω     29.00  73.00   0.50    6.19    --   -7.30  43.00  90.00   88
  7  ω     23.00  82.00   0.50    6.19    --   -7.30   0.00 -30.00  118
  8  ω    -82.00  82.00   0.50    6.19    --   -7.30  57.00 -60.00  328
  9  ω    -97.00  82.00   0.50    6.19    --   -7.30  29.00 -30.00  358
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0398580000
_diffrn_orient_matrix_UB_12      0.0534740000
_diffrn_orient_matrix_UB_13      0.0202815000
_diffrn_orient_matrix_UB_21      -0.0186170000
_diffrn_orient_matrix_UB_22      0.0941054000
_diffrn_orient_matrix_UB_23      -0.0143864000
_diffrn_orient_matrix_UB_31      -0.1009835000
_diffrn_orient_matrix_UB_32      0.0203438000
_diffrn_orient_matrix_UB_33      -0.0069978000
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_type              micromax007
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                10685
_reflns_number_total             11383
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         5.054
_refine_diff_density_min         -3.359
_refine_diff_density_rms         0.440
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     416
_refine_ls_number_reflns         11383
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0797
_refine_ls_R_factor_gt           0.0781
_refine_ls_restrained_S_all      1.106
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1972P)²+3.1503P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2361
_refine_ls_wR_factor_ref         0.2388
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.5853(17)
 0.4147(17)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C26(H26), C13(H13), C12(H12), C23(H23), C27(H27), C10(H10), C9(H9), C24(H24)
3.b Tetrahedral OH refined with riding coordinates:
 O3(H3), O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Au2 Au 1.58689(5) -0.31572(5) -0.02984(2) 0.02100(18) Uani 1 1 d . . . . .
Au1 Au -0.34039(5) 1.04863(6) 0.54136(2) 0.02125(18) Uani 1 1 d . . . . .
F1 F -0.3055(10) 0.9111(10) 0.6572(3) 0.0286(14) Uani 1 1 d . . . . .
F6 F 1.5573(10) -0.1724(10) -0.1464(2) 0.0276(13) Uani 1 1 d . . . . .
O4 O 0.6166(11) 0.3840(11) 0.1959(2) 0.0257(15) Uani 1 1 d . . . . .
O2 O 0.5757(11) 0.2671(11) 0.3153(2) 0.0243(14) Uani 1 1 d . . . . .
F7 F 1.8251(11) -0.3344(11) -0.2147(2) 0.0314(15) Uani 1 1 d . . . . .
F4 F -0.9276(9) 1.7061(10) 0.6150(2) 0.0358(15) Uani 1 1 d . . . . .
F10 F 2.0337(9) -0.7129(10) -0.0278(2) 0.0290(13) Uani 1 1 d . . . . .
F3 F -0.8418(10) 1.5086(11) 0.7089(2) 0.0374(15) Uani 1 1 d . . . . .
F9 F 2.3021(9) -0.8614(10) -0.0959(2) 0.0339(14) Uani 1 1 d . . . . .
F5 F -0.7178(10) 1.5073(11) 0.5428(2) 0.0340(14) Uani 1 1 d . . . . .
F8 F 2.1981(10) -0.6825(10) -0.1905(2) 0.0344(14) Uani 1 1 d . . . . .
N1 N -0.0718(12) 0.8207(13) 0.4584(3) 0.0198(16) Uani 1 1 d . . . . .
F2 F -0.5280(12) 1.1082(11) 0.7289(2) 0.0371(17) Uani 1 1 d . . . . .
C28 C 0.7765(14) 0.2126(15) 0.2046(3) 0.0207(18) Uani 1 1 d . . . . .
O3 O 0.8302(12) 0.1007(12) 0.2470(3) 0.0292(16) Uani 1 1 d . . . . .
H3 H 0.784869 0.178307 0.268664 0.044 Uiso 1 1 calc R . . . .
O1 O 0.3643(11) 0.5500(12) 0.2639(3) 0.0282(16) Uani 1 1 d . . . . .
H1 H 0.402871 0.471735 0.242348 0.042 Uiso 1 1 calc R . . . .
C16 C 1.7808(17) -0.4369(18) -0.0830(4) 0.022(2) Uani 1 1 d . . . . .
C1 C -0.1724(18) 0.9051(19) 0.4893(4) 0.024(2) Uani 1 1 d . . . . .
C17 C 1.7388(15) -0.3480(15) -0.1325(4) 0.0217(19) Uani 1 1 d . . . . .
N2 N 1.2987(13) -0.1227(13) 0.0537(3) 0.0228(17) Uani 1 1 d . . . . .
C3 C -0.4635(15) 1.1069(16) 0.6456(4) 0.0231(19) Uani 1 1 d . . . . .
C26 C 0.8477(14) 0.2112(15) 0.1173(3) 0.0203(17) Uani 1 1 d . . . . .
H26 H 0.712537 0.327178 0.110209 0.024 Uiso 1 1 calc R . . . .
C2 C -0.5060(17) 1.1972(18) 0.5959(4) 0.023(2) Uani 1 1 d . . . . .
C14 C 0.4169(13) 0.4388(14) 0.3065(3) 0.0171(16) Uani 1 1 d . . . . .
C21 C 1.9734(15) -0.6078(15) -0.0740(3) 0.0202(18) Uani 1 1 d . . . . .
C18 C 1.8721(15) -0.4266(16) -0.1682(4) 0.0235(19) Uani 1 1 d . . . . .
C20 C 2.1182(15) -0.6929(16) -0.1085(4) 0.025(2) Uani 1 1 d . . . . .
C22 C 1.1709(16) -0.0381(15) 0.0916(3) 0.0210(19) Uani 1 1 d . . . . .
C13 C 0.2116(15) 0.5208(15) 0.4309(3) 0.0231(19) Uani 1 1 d . . . . .
H13 H 0.240885 0.448512 0.463169 0.028 Uiso 1 1 calc R . . . .
C12 C 0.3307(15) 0.4300(15) 0.3935(3) 0.0210(18) Uani 1 1 d . . . . .
H12 H 0.446394 0.293984 0.400021 0.025 Uiso 1 1 calc R . . . .
C25 C 0.9163(14) 0.1243(14) 0.1648(3) 0.0206(17) Uani 1 1 d . . . . .
C23 C 1.2434(16) -0.1287(15) 0.1389(4) 0.024(2) Uani 1 1 d . . . . .
H23 H 1.378922 -0.244416 0.145775 0.029 Uiso 1 1 calc R . . . .
C8 C 0.0447(14) 0.7246(14) 0.4198(4) 0.0196(18) Uani 1 1 d . . . . .
C15 C 1.4014(19) -0.1932(19) 0.0223(4) 0.025(2) Uani 1 1 d . . . . .
C11 C 0.2835(13) 0.5356(14) 0.3462(3) 0.0200(17) Uani 1 1 d . . . . .
C27 C 0.9743(14) 0.1308(15) 0.0796(3) 0.0214(18) Uani 1 1 d . . . . .
H27 H 0.927962 0.189411 0.046625 0.026 Uiso 1 1 calc R . . . .
C10 C 0.1130(15) 0.7381(15) 0.3366(4) 0.0214(19) Uani 1 1 d . . . . .
H10 H 0.078213 0.808499 0.304166 0.026 Uiso 1 1 calc R . . . .
C19 C 2.0662(16) -0.6051(15) -0.1559(4) 0.025(2) Uani 1 1 d . . . . .
C7 C -0.6669(14) 1.3994(16) 0.5886(4) 0.0232(19) Uani 1 1 d . . . . .
C6 C -0.7774(15) 1.5063(16) 0.6251(4) 0.025(2) Uani 1 1 d . . . . .
C4 C -0.5744(16) 1.2050(16) 0.6825(4) 0.024(2) Uani 1 1 d . . . . .
C9 C -0.0042(15) 0.8355(16) 0.3739(4) 0.025(2) Uani 1 1 d . . . . .
H9 H -0.114874 0.974558 0.367963 0.030 Uiso 1 1 calc R . . . .
C24 C 1.1149(16) -0.0479(16) 0.1763(4) 0.024(2) Uani 1 1 d . . . . .
H24 H 1.160547 -0.108200 0.209262 0.028 Uiso 1 1 calc R . . . .
C5 C -0.7348(15) 1.4090(16) 0.6729(3) 0.0225(19) 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
Au2 C16 2.019(11) . ?
Au2 C15 1.970(11) . ?
Au1 C1 1.959(12) . ?
Au1 C2 2.022(11) . ?
F1 C3 1.349(12) . ?
F6 C17 1.353(11) . ?
O4 C28 1.242(12) . ?
O2 C14 1.240(11) . ?
F7 C18 1.342(12) . ?
F4 C6 1.347(12) . ?
F10 C21 1.365(11) . ?
F3 C5 1.333(11) . ?
F9 C20 1.334(11) . ?
F5 C7 1.362(12) . ?
F8 C19 1.333(11) . ?
N1 C1 1.163(14) . ?
N1 C8 1.408(12) . ?
F2 C4 1.349(12) . ?
C28 O3 1.292(12) . ?
C28 C25 1.489(13) . ?
O1 C14 1.293(12) . ?
C16 C17 1.411(15) . ?
C16 C21 1.367(15) . ?
C17 C18 1.365(14) . ?
N2 C22 1.402(12) . ?
N2 C15 1.151(15) . ?
C3 C2 1.419(16) . ?
C3 C4 1.359(15) . ?
C26 C25 1.374(14) . ?
C26 C27 1.385(13) . ?
C2 C7 1.380(15) . ?
C14 C11 1.481(12) . ?
C21 C20 1.390(13) . ?
C18 C19 1.406(14) . ?
C20 C19 1.359(15) . ?
C22 C23 1.378(15) . ?
C22 C27 1.388(14) . ?
C13 C12 1.375(13) . ?
C13 C8 1.408(13) . ?
C12 C11 1.392(13) . ?
C25 C24 1.404(14) . ?
C23 C24 1.387(14) . ?
C8 C9 1.370(15) . ?
C11 C10 1.408(13) . ?
C10 C9 1.383(14) . ?
C7 C6 1.371(14) . ?
C6 C5 1.386(15) . ?
C4 C5 1.390(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
C15 Au2 C16 178.5(4) . . ?
C1 Au1 C2 178.2(4) . . ?
C1 N1 C8 177.9(11) . . ?
O4 C28 O3 123.4(9) . . ?
O4 C28 C25 120.1(8) . . ?
O3 C28 C25 116.5(8) . . ?
C17 C16 Au2 124.0(8) . . ?
C21 C16 Au2 123.0(8) . . ?
C21 C16 C17 112.9(9) . . ?
N1 C1 Au1 179.5(10) . . ?
F6 C17 C16 119.4(9) . . ?
F6 C17 C18 116.5(9) . . ?
C18 C17 C16 124.1(9) . . ?
C15 N2 C22 178.8(11) . . ?
F1 C3 C2 118.5(10) . . ?
F1 C3 C4 117.6(9) . . ?
C4 C3 C2 123.8(10) . . ?
C25 C26 C27 120.5(9) . . ?
C3 C2 Au1 123.4(8) . . ?
C7 C2 Au1 123.2(9) . . ?
C7 C2 C3 113.4(10) . . ?
O2 C14 O1 123.4(8) . . ?
O2 C14 C11 120.5(8) . . ?
O1 C14 C11 115.9(8) . . ?
F10 C21 C16 119.4(9) . . ?
F10 C21 C20 114.7(8) . . ?
C16 C21 C20 125.9(9) . . ?
F7 C18 C17 121.6(9) . . ?
F7 C18 C19 119.1(9) . . ?
C17 C18 C19 119.3(9) . . ?
F9 C20 C21 121.1(9) . . ?
F9 C20 C19 120.2(9) . . ?
C19 C20 C21 118.6(9) . . ?
C23 C22 N2 118.9(9) . . ?
C23 C22 C27 122.9(9) . . ?
C27 C22 N2 118.2(9) . . ?
C12 C13 C8 117.8(9) . . ?
C13 C12 C11 120.6(9) . . ?
C26 C25 C28 119.4(8) . . ?
C26 C25 C24 121.0(9) . . ?
C24 C25 C28 119.6(9) . . ?
C22 C23 C24 118.8(9) . . ?
N1 C8 C13 117.8(9) . . ?
C9 C8 N1 118.8(8) . . ?
C9 C8 C13 123.4(9) . . ?
N2 C15 Au2 177.6(11) . . ?
C12 C11 C14 120.1(8) . . ?
C12 C11 C10 119.6(9) . . ?
C10 C11 C14 120.2(8) . . ?
C26 C27 C22 117.8(9) . . ?
C9 C10 C11 120.8(9) . . ?
F8 C19 C18 119.7(9) . . ?
F8 C19 C20 121.1(9) . . ?
C20 C19 C18 119.2(9) . . ?
F5 C7 C2 119.3(9) . . ?
F5 C7 C6 116.1(9) . . ?
C6 C7 C2 124.5(10) . . ?
F4 C6 C7 120.7(9) . . ?
F4 C6 C5 119.2(9) . . ?
C7 C6 C5 120.0(9) . . ?
F2 C4 C3 120.7(9) . . ?
F2 C4 C5 119.1(9) . . ?
C3 C4 C5 120.2(9) . . ?
C8 C9 C10 117.7(9) . . ?
C23 C24 C25 119.0(9) . . ?
F3 C5 C6 121.2(9) . . ?
F3 C5 C4 120.8(9) . . ?
C6 C5 C4 118.0(9) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 41.619
_oxdiff_exptl_absorpt_empirical_full_min 0.338
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.5853(17) 18393 6582 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000
0.0000 1.0000
2 0.4147(17) 18327 6582 nmt 0.0143 0.9181 0.0675 1.0144 -0.0821 0.0675 1.0126
0.9178 -0.9330

_twin_special_details            
;
Component 2 rotated by 179.9767° 
 around [0.58 0.58 0.58] (reciprocal) or [0.74 0.67 0.05] (direct)
;
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_kby-493_2
_database_code_depnum_ccdc_archive 'CCDC 1858876'
_audit_update_record             
;
2018-07-28 deposited with the CCDC.
2018-09-12 downloaded from the CCDC.
;
_audit_creation_date             2018-03-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        2B
_chemical_formula_moiety         'C13 H5 Au F5 N'
_chemical_formula_sum            'C13 H5 Au F5 N'
_chemical_formula_weight         467.15
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.2397(2)
_cell_length_b                   7.3439(2)
_cell_length_c                   12.3992(3)
_cell_angle_alpha                77.440(2)
_cell_angle_beta                 75.353(2)
_cell_angle_gamma                71.305(3)
_cell_volume                     597.43(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6841
_cell_measurement_temperature    123
_cell_measurement_theta_max      28.9250
_cell_measurement_theta_min      2.9330
_shelx_estimated_absorpt_T_max   0.478
_shelx_estimated_absorpt_T_min   0.102
_exptl_absorpt_coefficient_mu    12.363
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.19987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.597
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.856
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7833
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.856
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.895
_diffrn_reflns_theta_min         2.961
_diffrn_ambient_temperature      123
_diffrn_detector                 'PLATUS 200K area detector'
_diffrn_detector_area_resol_mean 5.811
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.856
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -33.00  -7.00   0.50    0.50    --   -7.30  27.00-116.00   52
  2  ω    -95.00 -68.00   0.50    0.50    --   -7.30  27.00-116.00   54
  3  ω    -63.00 -37.00   0.50    0.50    --    5.00  27.00-116.00   52
  4  ω    -97.00 -11.00   0.50    0.50    --   -7.30  60.00 150.00  172
  5  ω     -4.00  81.00   0.50    0.50    --   -7.30  60.00 150.00  170
  6  ω    -97.00 -66.00   0.50    0.50    --   -7.30  43.00  60.00   62
  7  ω    -57.00  82.00   0.50    0.50    --   -7.30  43.00  60.00  278
  8  ω     11.00  58.00   0.50    0.50    --   -7.30  27.00-116.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1030459000
_diffrn_orient_matrix_UB_12      0.0255397000
_diffrn_orient_matrix_UB_13      0.0241400000
_diffrn_orient_matrix_UB_21      -0.0069739000
_diffrn_orient_matrix_UB_22      -0.0876018000
_diffrn_orient_matrix_UB_23      -0.0117688000
_diffrn_orient_matrix_UB_31      0.0216301000
_diffrn_orient_matrix_UB_32      -0.0480179000
_diffrn_orient_matrix_UB_33      0.0534222000
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_type              micromax007
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2579
_reflns_number_total             2686
_reflns_odcompleteness_completeness 98.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.315
_refine_diff_density_min         -1.353
_refine_diff_density_rms         0.146
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2686
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0187
_refine_ls_R_factor_gt           0.0178
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0268P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0438
_refine_ls_wR_factor_ref         0.0440
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00C(H00C), C00D(H00D), C00F(H00F), C00J(H00J)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Au01 Au 0.40989(2) 0.25958(2) 0.42392(2) 0.01577(5) Uani 1 1 d . . . . .
F002 F -0.0556(3) 0.4238(3) 0.42399(15) 0.0231(4) Uani 1 1 d . . . . .
F003 F 0.5338(3) 0.1668(3) 0.16854(17) 0.0319(5) Uani 1 1 d . . . . .
F004 F -0.2668(3) 0.4710(3) 0.26730(17) 0.0272(4) Uani 1 1 d . . . . .
F005 F -0.0854(3) 0.3546(3) 0.06373(16) 0.0248(4) Uani 1 1 d . . . . .
F006 F 0.3169(3) 0.2085(3) 0.01480(16) 0.0296(5) Uani 1 1 d . . . . .
N007 N 0.6574(4) 0.2174(4) 0.6050(2) 0.0185(6) Uani 1 1 d . . . . .
C008 C 0.2498(5) 0.2922(4) 0.3042(3) 0.0157(6) Uani 1 1 d . . . . .
C009 C 0.0444(5) 0.3693(4) 0.3235(3) 0.0160(6) Uani 1 1 d . . . . .
C00A C 0.9801(5) 0.1311(4) 0.6512(3) 0.0194(6) Uani 1 1 d . . . . .
H00A H 1.040062 0.107043 0.576189 0.023 Uiso 1 1 calc R . . . .
C00B C 0.5658(5) 0.2325(5) 0.5387(3) 0.0203(7) Uani 1 1 d . . . . .
C00C C 1.0954(5) 0.1054(5) 0.7296(3) 0.0218(7) Uani 1 1 d . . . . .
H00C H 1.236232 0.061936 0.708958 0.026 Uiso 1 1 calc R . . . .
C00D C 0.6830(5) 0.2318(4) 0.7930(3) 0.0195(6) Uani 1 1 d . . . . .
H00D H 0.542149 0.275299 0.813678 0.023 Uiso 1 1 calc R . . . .
C00E C -0.0679(5) 0.3937(4) 0.2442(3) 0.0161(6) Uani 1 1 d . . . . .
C00F C 1.0060(6) 0.1430(5) 0.8385(3) 0.0231(7) Uani 1 1 d . . . . .
H00F H 1.086205 0.125263 0.891976 0.028 Uiso 1 1 calc R . . . .
C00G C 0.7751(5) 0.1927(4) 0.6844(3) 0.0154(6) Uani 1 1 d . . . . .
C00H C 0.3343(5) 0.2426(4) 0.1978(3) 0.0190(6) Uani 1 1 d . . . . .
C00I C 0.0236(5) 0.3367(4) 0.1404(3) 0.0160(6) Uani 1 1 d . . . . .
C00J C 0.8005(5) 0.2062(5) 0.8700(3) 0.0225(7) Uani 1 1 d . . . . .
H00J H 0.740683 0.231977 0.944752 0.027 Uiso 1 1 calc R . . . .
C00K C 0.2262(5) 0.2635(4) 0.1162(3) 0.0181(6) 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
Au01 C008 2.035(3) . ?
Au01 C00B 1.971(4) . ?
F002 C009 1.346(4) . ?
F003 C00H 1.355(4) . ?
F004 C00E 1.348(4) . ?
F005 C00I 1.342(3) . ?
F006 C00K 1.345(4) . ?
N007 C00B 1.148(5) . ?
N007 C00G 1.405(4) . ?
C008 C009 1.389(5) . ?
C008 C00H 1.381(5) . ?
C009 C00E 1.377(4) . ?
C00A H00A 0.9500 . ?
C00A C00C 1.381(4) . ?
C00A C00G 1.385(5) . ?
C00C H00C 0.9500 . ?
C00C C00F 1.387(5) . ?
C00D H00D 0.9500 . ?
C00D C00G 1.389(5) . ?
C00D C00J 1.379(4) . ?
C00E C00I 1.377(5) . ?
C00F H00F 0.9500 . ?
C00F C00J 1.387(5) . ?
C00H C00K 1.384(4) . ?
C00I C00K 1.369(5) . ?
C00J H00J 0.9500 . ?

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
C00B Au01 C008 178.98(11) . . ?
C00B N007 C00G 177.7(4) . . ?
C009 C008 Au01 122.0(2) . . ?
C00H C008 Au01 123.5(3) . . ?
C00H C008 C009 114.5(3) . . ?
F002 C009 C008 120.2(3) . . ?
F002 C009 C00E 116.4(3) . . ?
C00E C009 C008 123.3(3) . . ?
C00C C00A H00A 120.8 . . ?
C00C C00A C00G 118.5(3) . . ?
C00G C00A H00A 120.8 . . ?
N007 C00B Au01 179.6(4) . . ?
C00A C00C H00C 119.9 . . ?
C00A C00C C00F 120.2(3) . . ?
C00F C00C H00C 119.9 . . ?
C00G C00D H00D 120.7 . . ?
C00J C00D H00D 120.7 . . ?
C00J C00D C00G 118.6(3) . . ?
F004 C00E C009 120.7(3) . . ?
F004 C00E C00I 119.6(3) . . ?
C009 C00E C00I 119.7(3) . . ?
C00C C00F H00F 119.7 . . ?
C00J C00F C00C 120.6(3) . . ?
C00J C00F H00F 119.7 . . ?
C00A C00G N007 118.6(3) . . ?
C00A C00G C00D 122.1(3) . . ?
C00D C00G N007 119.3(3) . . ?
F003 C00H C008 120.1(3) . . ?
F003 C00H C00K 116.1(3) . . ?
C008 C00H C00K 123.8(3) . . ?
F005 C00I C00E 120.1(3) . . ?
F005 C00I C00K 120.6(3) . . ?
C00K C00I C00E 119.3(3) . . ?
C00D C00J C00F 120.0(3) . . ?
C00D C00J H00J 120.0 . . ?
C00F C00J H00J 120.0 . . ?
F006 C00K C00H 121.0(3) . . ?
F006 C00K C00I 119.7(3) . . ?
C00I C00K C00H 119.3(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.978
_oxdiff_exptl_absorpt_empirical_full_min 0.645
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_ming_red
_database_code_depnum_ccdc_archive 'CCDC 1858875'
_audit_update_record             
;
2018-07-28 deposited with the CCDC.
2018-09-12 downloaded from the CCDC.
;
_audit_creation_date             2018-01-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        1R
_chemical_formula_moiety         'C14 H5 Au F5 N O2'
_chemical_formula_sum            'C14 H5 Au F5 N O2'
_chemical_formula_weight         511.16
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C14 H5 Au F5 N O2'
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'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 1 2/c 1'
_space_group_name_Hall           '-P 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   13.4101(9)
_cell_length_b                   7.7601(5)
_cell_length_c                   13.0837(12)
_cell_angle_alpha                90
_cell_angle_beta                 97.493(7)
_cell_angle_gamma                90
_cell_volume                     1349.91(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4246
_cell_measurement_temperature    93
_cell_measurement_theta_max      74.0380
_cell_measurement_theta_min      6.4820
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    21.167
_exptl_absorpt_correction_T_max  0.44676
_exptl_absorpt_correction_T_min  0.39681
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.42a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.515
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             944
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 4 -5 0.0547
0 -2 -8 0.0407
0 3 7 0.0201
1 2 -8 0.0543
9 0 -1 0.0108
0 -5 2 0.0346
-9 0 1 0.0126

_exptl_crystal_size_max          0.101
_exptl_crystal_size_mid          0.069
_exptl_crystal_size_min          0.024
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
0.2007 4.0627 -4.9964 0.4558 0.0641 0.8878
0.2590 -1.6106 -8.0030 -0.7002 -0.0984 0.7071
-0.2051 3.0372 6.7373 0.8857 0.1245 -0.4472
1.1385 2.2217 -7.6151 -0.0138 0.0985 0.9950
8.7029 -0.0317 -0.8208 -0.1392 0.9903 -0.0000
0.0051 -5.0032 2.0781 -0.7746 -0.0956 -0.6621
-8.9650 -0.0093 0.9563 0.1417 -1.0198 -0.0155

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0871
_diffrn_reflns_av_unetI/netI     0.0613
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6129
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.043
_diffrn_reflns_theta_max         67.043
_diffrn_reflns_theta_min         5.701
_diffrn_ambient_temperature      93
_diffrn_detector                 'PLATUS 200K area detector'
_diffrn_detector_area_resol_mean 5.811
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -37.00   9.00   0.50    0.52    --  -43.40  57.00  90.00   92
  2  ω   -115.00 -68.00   0.50    0.52    --  -43.40 -72.00 -30.00   94
  3  ω     12.00  44.00   0.50    0.52    --  -43.40  57.00  90.00   64
  4  ω    -56.00 -22.00   0.50    0.52    --  -43.40 -72.00 -30.00   68
  5  ω    -74.00  44.00   0.50    0.52    --  -43.40  57.00-150.00  236
  6  ω   -111.00 -85.00   0.50    2.10    -- -107.60 -72.00  30.00   52
  7  ω   -136.00 -18.00   0.50    2.10    -- -107.60  57.00   0.00  236
  8  ω   -197.00-112.00   0.50    2.10    -- -107.60 -72.00  30.00  170
  9  ω   -194.00-120.00   0.50    2.10    -- -107.60 -57.00   0.00  148
 10  ω    -83.00 -31.00   0.50    2.10    -- -107.60  72.00 -60.00  104
 11  ω   -112.00 -86.00   0.50    2.10    -- -107.60 -72.00  90.00   52
 12  ω   -147.00 -92.00   0.50    2.10    -- -107.60  72.00 -60.00  110
 13  ω    -78.00 -23.00   0.50    2.10    -- -107.60 -19.00 -60.00  110
 14  ω   -156.00 -74.00   0.50    2.10    -- -107.60 -38.00  90.00  164
 15  ω   -192.00-181.00   0.50    2.10    -- -107.60 -72.00  90.00   22
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0104744000
_diffrn_orient_matrix_UB_12      0.1762752000
_diffrn_orient_matrix_UB_13      0.0516803000
_diffrn_orient_matrix_UB_21      0.1149301000
_diffrn_orient_matrix_UB_22      0.0238793000
_diffrn_orient_matrix_UB_23      0.0112104000
_diffrn_orient_matrix_UB_31      -0.0097147000
_diffrn_orient_matrix_UB_32      0.0881318000
_diffrn_orient_matrix_UB_33      -0.1064059000
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_type              FR
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2227
_reflns_number_total             2394
_reflns_odcompleteness_completeness 99.16
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.42a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.42a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.42a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         3.456
_refine_diff_density_min         -2.815
_refine_diff_density_rms         0.430
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2394
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0633
_refine_ls_restrained_S_all      1.101
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1585P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1704
_refine_ls_wR_factor_ref         0.1942
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C2(H2A), C3(H3)
2.b Tetrahedral OH refined with riding coordinates:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Au1 Au 0.53896(2) 0.55133(4) 0.36361(3) 0.0231(3) Uani 1 1 d . . . . .
F5 F 0.5538(5) 0.1350(8) 0.3591(4) 0.0285(13) Uani 1 1 d . . . . .
F4 F 0.7032(6) -0.0732(7) 0.3317(5) 0.0320(15) Uani 1 1 d . . . . .
F1 F 0.7644(4) 0.6118(8) 0.3171(5) 0.0329(13) Uani 1 1 d . . . . .
F2 F 0.9143(4) 0.3992(10) 0.2945(5) 0.0372(14) Uani 1 1 d . . . . .
F3 F 0.8879(5) 0.0520(6) 0.3071(6) 0.0333(16) Uani 1 1 d . . . . .
O2 O 0.0126(5) 1.2748(8) 0.4988(5) 0.0281(14) Uani 1 1 d . . . . .
H2 H -0.025712 1.355544 0.504491 0.042 Uiso 1 1 calc R . . . .
O1 O 0.1149(5) 1.4857(8) 0.4656(5) 0.0224(13) Uani 1 1 d . . . . .
N1 N 0.3763(7) 0.8272(11) 0.3986(6) 0.0255(18) Uani 1 1 d . . . . .
C9 C 0.6514(6) 0.3862(13) 0.3414(7) 0.0212(18) Uani 1 1 d . . . . .
C8 C 0.4369(7) 0.7228(14) 0.3854(7) 0.028(2) Uani 1 1 d . . . . .
C14 C 0.6412(6) 0.2092(13) 0.3414(7) 0.0247(18) Uani 1 1 d . . . . .
C4 C 0.1677(6) 1.1950(11) 0.4497(7) 0.0195(17) Uani 1 1 d . . . . .
C6 C 0.3360(7) 1.1202(14) 0.4279(7) 0.025(2) Uani 1 1 d . . . . .
H6 H 0.402643 1.150855 0.425223 0.030 Uiso 1 1 calc R . . . .
C5 C 0.2668(7) 1.2453(12) 0.4454(7) 0.0223(17) Uani 1 1 d . . . . .
H5 H 0.285895 1.360085 0.453981 0.027 Uiso 1 1 calc R . . . .
C10 C 0.7467(9) 0.4407(10) 0.3212(9) 0.024(2) Uani 1 1 d . . . . .
C1 C 0.3067(9) 0.9486(11) 0.4142(8) 0.025(2) Uani 1 1 d . . . . .
C2 C 0.2068(7) 0.9007(14) 0.4159(8) 0.0226(19) Uani 1 1 d . . . . .
H2A H 0.187191 0.786387 0.405954 0.027 Uiso 1 1 calc R . . . .
C7 C 0.0949(6) 1.3320(11) 0.4714(7) 0.0203(18) Uani 1 1 d . . . . .
C13 C 0.7178(8) 0.0989(14) 0.3299(7) 0.0211(19) Uani 1 1 d . . . . .
C11 C 0.8243(7) 0.3327(13) 0.3104(7) 0.027(2) Uani 1 1 d . . . . .
C3 C 0.1375(7) 1.0256(13) 0.4327(8) 0.024(2) Uani 1 1 d . . . . .
H3 H 0.070342 0.995842 0.432623 0.028 Uiso 1 1 calc R . . . .
C12 C 0.8122(7) 0.1577(13) 0.3160(7) 0.025(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 Au1 3.0198(7) 2_655 ?
Au1 C9 2.028(9) . ?
Au1 C8 1.956(10) . ?
F5 C14 1.353(11) . ?
F4 C13 1.350(11) . ?
F1 C10 1.351(10) . ?
F2 C11 1.354(11) . ?
F3 C12 1.322(11) . ?
O2 H2 0.8200 . ?
O2 C7 1.282(11) . ?
O1 C7 1.227(11) . ?
N1 C8 1.176(13) . ?
N1 C1 1.360(14) . ?
C9 C14 1.380(15) . ?
C9 C10 1.404(15) . ?
C14 C13 1.360(14) . ?
C4 C5 1.393(13) . ?
C4 C7 1.496(12) . ?
C4 C3 1.385(13) . ?
C6 H6 0.9300 . ?
C6 C5 1.382(13) . ?
C6 C1 1.393(15) . ?
C5 H5 0.9300 . ?
C10 C11 1.357(14) . ?
C1 C2 1.393(15) . ?
C2 H2A 0.9300 . ?
C2 C3 1.380(15) . ?
C13 C12 1.380(15) . ?
C11 C12 1.371(15) . ?
C3 H3 0.9300 . ?

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 Au1 91.6(3) . 2_655 ?
C8 Au1 Au1 89.1(3) . 2_655 ?
C8 Au1 C9 176.3(4) . . ?
C7 O2 H2 109.5 . . ?
C8 N1 C1 179.6(12) . . ?
C14 C9 Au1 123.6(6) . . ?
C14 C9 C10 113.1(8) . . ?
C10 C9 Au1 123.3(7) . . ?
N1 C8 Au1 179.3(9) . . ?
F5 C14 C9 120.7(8) . . ?
F5 C14 C13 115.8(9) . . ?
C13 C14 C9 123.4(9) . . ?
C5 C4 C7 117.3(7) . . ?
C3 C4 C5 121.3(8) . . ?
C3 C4 C7 121.4(8) . . ?
C5 C6 H6 119.7 . . ?
C5 C6 C1 120.6(9) . . ?
C1 C6 H6 119.7 . . ?
C4 C5 H5 120.8 . . ?
C6 C5 C4 118.3(9) . . ?
C6 C5 H5 120.8 . . ?
F1 C10 C9 118.2(9) . . ?
F1 C10 C11 117.5(10) . . ?
C11 C10 C9 124.2(8) . . ?
N1 C1 C6 119.6(10) . . ?
N1 C1 C2 119.8(9) . . ?
C6 C1 C2 120.5(10) . . ?
C1 C2 H2A 120.5 . . ?
C3 C2 C1 119.0(10) . . ?
C3 C2 H2A 120.5 . . ?
O2 C7 C4 114.5(7) . . ?
O1 C7 O2 123.8(8) . . ?
O1 C7 C4 121.7(8) . . ?
F4 C13 C14 120.5(10) . . ?
F4 C13 C12 117.8(9) . . ?
C14 C13 C12 121.7(10) . . ?
F2 C11 C10 119.4(9) . . ?
F2 C11 C12 120.0(9) . . ?
C10 C11 C12 120.6(9) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 C4 120.2(9) . . ?
C2 C3 H3 119.9 . . ?
F3 C12 C13 122.4(9) . . ?
F3 C12 C11 120.8(9) . . ?
C11 C12 C13 116.8(9) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.543
_oxdiff_exptl_absorpt_empirical_full_min 0.600
_exptl_crystal_preparation       Luminescent
