# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_eat-156-p1_b
_database_code_depnum_ccdc_archive 'CCDC 1443527'
_audit_update_record             
;
2015-12-21 deposited with the CCDC.
2016-05-31 downloaded from the CCDC.
;
_audit_creation_date             2015-12-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            'Tolylpyridine methyl acetonitrile gold(III)'
_chemical_name_systematic        
"'[2-(4-tolyl)pyridine-κ²N,C⁷](acetonitrile-\kN)methylgold(III) tetrafluoroborate'"
_chemical_formula_moiety         '(C15 H16 Au N2 1+), (B F4 1-)'
_chemical_formula_sum            'C15 H16 Au B F4 N2'
_chemical_formula_weight         508.07
_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'
B B 0.0013 0.0007 '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      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 1 21/m 1'
_space_group_name_Hall           '-P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   10.2527(5)
_cell_length_b                   6.6903(3)
_cell_length_c                   12.3307(6)
_cell_angle_alpha                90
_cell_angle_beta                 109.737(2)
_cell_angle_gamma                90
_cell_volume                     796.12(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    292
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      21.411
_cell_measurement_theta_min      2.110
_shelx_estimated_absorpt_T_max   0.524
_shelx_estimated_absorpt_T_min   0.258
_exptl_absorpt_coefficient_mu    9.279
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.119
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   0.7454
_exptl_transmission_factor_min   0.4424
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12713
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.448
_diffrn_reflns_theta_min         2.110
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  
'Bruker D8 Venture fixed-chi goniometer and Photon100 CMOS detector'
_diffrn_measurement_method       'profile data from φ and ω scans'
_diffrn_detector_area_resol_mean 10.4167
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1751
_reflns_number_total             1786
_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       'APEX2 v2013.6--2 (Bruker AXS)'
_computing_data_collection       'APEX2 v2013.6--2 (Bruker AXS)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Diamond v3.2i (Brandenburg, 2012)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         1.131
_refine_diff_density_min         -0.727
_refine_diff_density_rms         0.122
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     142
_refine_ls_number_reflns         1786
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0229
_refine_ls_R_factor_gt           0.0221
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+6.5544P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0504
_refine_ls_wR_factor_ref         0.0507
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H1A(0.5) H1B(0.5) H1C(0.5) H15A(0.5) H15B(0.5) H15C(0.5) H7A(0.5)
 H7B(0.5) H7C(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C10(H10), C13(H13), C8(H8), C11(H11), C5(H5)
3.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C15(H15A,H15B,H15C), C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Au1 Au 0.29330(2) 0.2500 0.42488(2) 0.01491(8) Uani 1 2 d S T P . .
N1 N 0.1359(5) 0.2500 0.2644(4) 0.0203(11) Uani 1 2 d S T P . .
N2 N 0.4566(5) 0.2500 0.3565(4) 0.0144(10) Uani 1 2 d S T P . .
C1 C 0.1458(6) 0.2500 0.5030(6) 0.0253(14) Uani 1 2 d S T P . .
H1A H 0.1743 0.1595 0.5694 0.038 Uiso 0.5 1 calc GR . . A -1
H1B H 0.0572 0.2049 0.4480 0.038 Uiso 0.5 1 calc GR . . A -1
H1C H 0.1353 0.3856 0.5290 0.038 Uiso 0.5 1 calc GR . . A -1
C4 C 0.7031(6) 0.2500 0.6544(5) 0.0178(12) Uani 1 2 d S T P . .
H4 H 0.7910 0.2500 0.6445 0.021 Uiso 1 2 calc RS T P . .
C15 C -0.0606(6) 0.2500 0.0682(5) 0.0214(13) Uani 1 2 d S T P . .
H15A H -0.1369 0.3341 0.0726 0.032 Uiso 0.5 1 calc GR . . B -1
H15B H -0.0939 0.1131 0.0481 0.032 Uiso 0.5 1 calc GR . . B -1
H15C H -0.0256 0.3029 0.0092 0.032 Uiso 0.5 1 calc GR . . B -1
C14 C 0.0484(6) 0.2500 0.1773(5) 0.0151(12) Uani 1 2 d S T P . .
C2 C 0.4513(6) 0.2500 0.5745(5) 0.0150(11) Uani 1 2 d S T P . .
C10 C 0.4451(7) 0.2500 0.2451(5) 0.0197(13) Uani 1 2 d S T P . .
H10 H 0.3556 0.2500 0.1879 0.024 Uiso 1 2 calc RS T P . .
C6 C 0.5667(6) 0.2500 0.7809(5) 0.0193(13) Uani 1 2 d S T P . .
C3 C 0.5813(6) 0.2500 0.5574(5) 0.0144(11) Uani 1 2 d S T P . .
C7 C 0.5593(6) 0.2500 0.9015(5) 0.0235(14) Uani 1 2 d S T P . .
H7A H 0.4639 0.2229 0.8977 0.035 Uiso 0.5 1 calc GR . . C -1
H7B H 0.5883 0.3808 0.9373 0.035 Uiso 0.5 1 calc GR . . C -1
H7C H 0.6208 0.1463 0.9476 0.035 Uiso 0.5 1 calc GR . . C -1
C9 C 0.5829(6) 0.2500 0.4390(5) 0.0147(11) Uani 1 2 d S T P . .
C13 C 0.7030(7) 0.2500 0.4095(5) 0.0191(12) Uani 1 2 d S T P . .
H13 H 0.7918 0.2500 0.4678 0.023 Uiso 1 2 calc RS T P . .
C12 C 0.6909(7) 0.2500 0.2947(6) 0.0233(14) Uani 1 2 d S T P . .
C8 C 0.4461(6) 0.2500 0.6850(5) 0.0158(12) Uani 1 2 d S T P . .
H8 H 0.3586 0.2500 0.6958 0.019 Uiso 1 2 calc RS T P . .
C11 C 0.5614(7) 0.2500 0.2116(5) 0.0249(14) Uani 1 2 d S T P . .
H11 H 0.5517 0.2500 0.1322 0.030 Uiso 1 2 calc RS T P . .
C5 C 0.6948(6) 0.2500 0.7646(5) 0.0184(12) Uani 1 2 d S T P . .
H5 H 0.7775 0.2500 0.8297 0.022 Uiso 1 2 calc RS T P . .
F1 F 0.7942(4) 0.5837(5) 0.1781(4) 0.0611(11) Uani 1 1 d . . . . .
F3 F 0.7865(5) 0.7500 0.0174(4) 0.0530(14) Uani 1 2 d S T P . .
F2 F 0.9805(4) 0.7500 0.1677(4) 0.0579(16) Uani 1 2 d S T P . .
B1 B 0.8387(8) 0.7500 0.1369(6) 0.0234(15) Uani 1 2 d S T P . .
H12 H 0.766(7) 0.2500 0.264(5) 0.014(16) Uiso 1 2 d S T P . .


_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 N1 2.088(5) . ?
Au1 N2 2.113(5) . ?
Au1 C1 2.049(6) . ?
Au1 C2 2.002(6) . ?
N1 C14 1.144(8) . ?
N2 C10 1.339(7) . ?
N2 C9 1.350(7) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C4 H4 0.9500 . ?
C4 C3 1.407(8) . ?
C4 C5 1.390(8) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C15 C14 1.428(8) . ?
C2 C3 1.418(8) . ?
C2 C8 1.382(8) . ?
C10 H10 0.9500 . ?
C10 C11 1.387(9) . ?
C6 C7 1.514(8) . ?
C6 C8 1.392(8) . ?
C6 C5 1.394(8) . ?
C3 C9 1.465(8) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C9 C13 1.397(8) . ?
C13 H13 0.9500 . ?
C13 C12 1.379(8) . ?
C12 C11 1.377(10) . ?
C12 H12 0.96(7) . ?
C8 H8 0.9500 . ?
C11 H11 0.9500 . ?
C5 H5 0.9500 . ?
F1 B1 1.364(5) . ?
F3 B1 1.387(9) . ?
F2 B1 1.373(9) . ?
B1 F1 1.364(5) 4_575 ?

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
N1 Au1 N2 94.87(19) . . ?
C1 Au1 N1 89.3(2) . . ?
C1 Au1 N2 175.8(2) . . ?
C2 Au1 N1 177.0(2) . . ?
C2 Au1 N2 82.2(2) . . ?
C2 Au1 C1 93.6(2) . . ?
C14 N1 Au1 179.0(5) . . ?
C10 N2 Au1 127.0(4) . . ?
C10 N2 C9 120.2(5) . . ?
C9 N2 Au1 112.8(4) . . ?
Au1 C1 H1A 109.5 . . ?
Au1 C1 H1B 109.5 . . ?
Au1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C5 C4 C3 120.1(5) . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
N1 C14 C15 179.8(6) . . ?
C3 C2 Au1 111.9(4) . . ?
C8 C2 Au1 128.3(4) . . ?
C8 C2 C3 119.8(5) . . ?
N2 C10 H10 119.4 . . ?
N2 C10 C11 121.3(6) . . ?
C11 C10 H10 119.4 . . ?
C8 C6 C7 120.6(5) . . ?
C8 C6 C5 119.2(5) . . ?
C5 C6 C7 120.2(5) . . ?
C4 C3 C2 118.9(5) . . ?
C4 C3 C9 122.8(5) . . ?
C2 C3 C9 118.3(5) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C9 C3 114.9(5) . . ?
N2 C9 C13 120.6(5) . . ?
C13 C9 C3 124.5(5) . . ?
C9 C13 H13 120.5 . . ?
C12 C13 C9 119.1(6) . . ?
C12 C13 H13 120.5 . . ?
C13 C12 H12 126(4) . . ?
C11 C12 C13 119.6(6) . . ?
C11 C12 H12 114(4) . . ?
C2 C8 C6 121.2(6) . . ?
C2 C8 H8 119.4 . . ?
C6 C8 H8 119.4 . . ?
C10 C11 H11 120.4 . . ?
C12 C11 C10 119.3(6) . . ?
C12 C11 H11 120.4 . . ?
C4 C5 C6 120.8(5) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
F1 B1 F1 109.3(6) 4_575 . ?
F1 B1 F3 109.8(4) 4_575 . ?
F1 B1 F3 109.8(4) . . ?
F1 B1 F2 110.7(4) . . ?
F1 B1 F2 110.7(4) 4_575 . ?
F2 B1 F3 106.6(6) . . ?

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
Au1 N2 C10 C11 180.000(1) . . . . ?
Au1 N2 C9 C3 0.000(1) . . . . ?
Au1 N2 C9 C13 180.000(1) . . . . ?
Au1 C2 C3 C4 180.000(2) . . . . ?
Au1 C2 C3 C9 0.000(2) . . . . ?
Au1 C2 C8 C6 180.000(2) . . . . ?
N2 C10 C11 C12 0.000(1) . . . . ?
N2 C9 C13 C12 0.000(2) . . . . ?
C4 C3 C9 N2 180.000(2) . . . . ?
C4 C3 C9 C13 0.000(2) . . . . ?
C2 C3 C9 N2 0.000(2) . . . . ?
C2 C3 C9 C13 180.000(2) . . . . ?
C10 N2 C9 C3 180.000(2) . . . . ?
C10 N2 C9 C13 0.000(2) . . . . ?
C3 C4 C5 C6 0.000(3) . . . . ?
C3 C2 C8 C6 0.000(3) . . . . ?
C3 C9 C13 C12 180.000(2) . . . . ?
C7 C6 C8 C2 180.000(3) . . . . ?
C7 C6 C5 C4 180.000(3) . . . . ?
C9 N2 C10 C11 0.000(1) . . . . ?
C9 C13 C12 C11 0.000(2) . . . . ?
C13 C12 C11 C10 0.000(1) . . . . ?
C8 C2 C3 C4 0.000(3) . . . . ?
C8 C2 C3 C9 180.000(2) . . . . ?
C8 C6 C5 C4 0.000(3) . . . . ?
C5 C4 C3 C2 0.000(3) . . . . ?
C5 C4 C3 C9 180.000(2) . . . . ?
C5 C6 C8 C2 0.000(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_msh-246-mp_sx
_database_code_depnum_ccdc_archive 'CCDC 1443528'
_audit_update_record             
;
2015-12-21 deposited with the CCDC.
2016-05-31 downloaded from the CCDC.
;
_audit_creation_date             2015-12-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H18 Au N2 O, C2 F3 O2'
_chemical_formula_sum            'C18 H18 Au F3 N2 O3'
_chemical_formula_weight         564.31
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           14
_space_group_name_H-M_alt        'P 1 1 21/n'
_space_group_name_Hall           '-P 2n'
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                   7.1906(6)
_cell_length_b                   12.6491(10)
_cell_length_c                   19.3960(16)
_cell_angle_alpha                90
_cell_angle_beta                 89.9973(16)
_cell_angle_gamma                90
_cell_volume                     1764.2(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9860
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.64
_cell_measurement_theta_min      2.65
_shelx_estimated_absorpt_T_max   0.564
_shelx_estimated_absorpt_T_min   0.110
_exptl_absorpt_coefficient_mu    8.391
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.3406
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1022 before and 0.0516 after correction.
The Ratio of minimum to maximum transmission is 0.4564.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.125
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.472
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.077
_exptl_transmission_factor_max   1.0000
_exptl_transmission_factor_min   0.4564
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            28613
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.617
_diffrn_reflns_theta_min         2.646
_diffrn_ambient_temperature      100.01
_diffrn_detector                 'Bruker PHOTON100 area detector'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture, CMOS detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5610
_reflns_number_total             5951
_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       'APEX2 v2014.11-0 (Bruker-AXS, 2014)'
_computing_data_collection       'APEX2 v2014.11-0 (Bruker-AXS, 2014)'
_computing_data_reduction        'SAINT v8.34A (Bruker-AXS, 2014)'
_computing_molecular_graphics    'Diamond v4.0.1 (Brandenburg, 2014)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.789
_refine_diff_density_min         -1.515
_refine_diff_density_rms         0.140
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         5951
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0214
_refine_ls_R_factor_gt           0.0187
_refine_ls_restrained_S_all      1.050
_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)+(0.0043P)²+0.9651P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0415
_refine_ls_wR_factor_ref         0.0424
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.5112(6) 0.4888(6)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C17(H17A,H17B)
3.b Aromatic/amide H refined with riding coordinates:
 N5(H5), C10(H10), C11(H11), C12(H12), C18(H18), C7(H7), C13(H13), C15(H15)
3.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Au1 Au 0.68928(2) 0.10218(2) 0.47359(2) 0.00950(3) Uani 1 1 d . . . . .
N1 N 0.7333(3) 0.07202(19) 0.58021(12) 0.0122(5) Uani 1 1 d . . . . .
C4 C 0.6557(4) 0.1123(2) 0.36924(13) 0.0136(5) Uani 1 1 d . . . . .
H4A H 0.7788 0.1065 0.3467 0.016 Uiso 1 1 calc R . . . .
H4B H 0.5783 0.0523 0.3533 0.016 Uiso 1 1 calc R . . . .
N5 N 0.6434(4) 0.2651(2) 0.48145(12) 0.0145(5) Uani 1 1 d . . . . .
H5 H 0.6002 0.2889 0.5210 0.017 Uiso 1 1 calc R . . . .
C9 C 0.7604(4) -0.0520(2) 0.46849(15) 0.0115(5) Uani 1 1 d . . . . .
C10 C 0.7704(4) -0.1147(2) 0.40976(14) 0.0150(6) Uani 1 1 d . . . . .
H10 H 0.7382 -0.0851 0.3664 0.018 Uiso 1 1 calc R . . . .
C11 C 0.8351(4) -0.0567(2) 0.66133(15) 0.0155(6) Uani 1 1 d . . . . .
H11 H 0.8834 -0.1251 0.6706 0.019 Uiso 1 1 calc R . . . .
C12 C 0.8035(5) 0.0135(2) 0.71486(14) 0.0167(5) Uani 1 1 d . . . . .
H12 H 0.8292 -0.0067 0.7611 0.020 Uiso 1 1 calc R . . . .
C14 C 0.7957(4) -0.0266(2) 0.59375(13) 0.0113(5) Uani 1 1 d . . . . .
C18 C 0.7013(5) 0.1406(2) 0.63205(14) 0.0141(5) Uani 1 1 d . . . . .
H18 H 0.6551 0.2091 0.6216 0.017 Uiso 1 1 calc R . . . .
C2 C 0.8121(5) -0.0954(3) 0.53269(12) 0.0127(4) Uani 1 1 d . . . . .
C6 C 0.8268(5) -0.2205(2) 0.41316(15) 0.0158(5) Uani 1 1 d . . . . .
C7 C 0.7343(4) 0.1134(3) 0.70065(14) 0.0185(6) Uani 1 1 d . . . . .
H7 H 0.7099 0.1622 0.7368 0.022 Uiso 1 1 calc R . . . .
C13 C 0.8774(5) -0.2616(3) 0.47711(16) 0.0183(6) Uani 1 1 d . . . . .
H13 H 0.9171 -0.3331 0.4802 0.022 Uiso 1 1 calc R . . . .
C8 C 0.8314(6) -0.2877(2) 0.34914(16) 0.0221(7) Uani 1 1 d . . . . .
H8A H 0.8906 -0.2482 0.3116 0.033 Uiso 1 1 calc GR . . . .
H8B H 0.7041 -0.3064 0.3358 0.033 Uiso 1 1 calc GR . . . .
H8C H 0.9024 -0.3523 0.3583 0.033 Uiso 1 1 calc GR . . . .
O2 O 0.6678(3) 0.30875(17) 0.36693(10) 0.0175(4) Uani 1 1 d . . . . .
C3 C 0.6728(6) 0.3334(2) 0.43370(14) 0.0135(6) Uani 1 1 d . . . . .
C15 C 0.8709(4) -0.2000(3) 0.53642(16) 0.0156(6) Uani 1 1 d . . . . .
H15 H 0.9067 -0.2294 0.5795 0.019 Uiso 1 1 calc R . . . .
C16 C 0.7199(6) 0.4479(3) 0.44533(18) 0.0215(9) Uani 1 1 d . . . . .
H16A H 0.7377 0.4605 0.4947 0.032 Uiso 1 1 calc GR . . . .
H16B H 0.6181 0.4923 0.4283 0.032 Uiso 1 1 calc GR . . . .
H16C H 0.8346 0.4654 0.4205 0.032 Uiso 1 1 calc GR . . . .
C17 C 0.5649(5) 0.2147(2) 0.34783(14) 0.0151(5) Uani 1 1 d . . . . .
H17A H 0.5484 0.2143 0.2972 0.018 Uiso 1 1 calc R . . . .
H17B H 0.4397 0.2184 0.3689 0.018 Uiso 1 1 calc R . . . .
F19 F 0.6829(4) 0.58248(15) 0.72531(12) 0.0399(6) Uani 1 1 d . . . . .
O1A O 0.6484(5) 0.3918(2) 0.60422(12) 0.0379(7) Uani 1 1 d . . . . .
O1B O 0.6425(4) 0.36648(19) 0.71806(12) 0.0270(6) Uani 1 1 d . . . . .
C1C C 0.6767(5) 0.4155(2) 0.66527(14) 0.0172(6) Uani 1 1 d . . . . .
F1D F 0.7667(4) 0.5866(2) 0.62060(13) 0.0548(9) Uani 1 1 d . . . . .
F1E F 0.9426(4) 0.5169(2) 0.69687(17) 0.0524(8) Uani 1 1 d . . . . .
C1F C 0.7680(5) 0.5261(3) 0.67682(17) 0.0206(7) 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 N1 2.126(2) . ?
Au1 C4 2.042(3) . ?
Au1 N5 2.092(3) . ?
Au1 C9 2.019(3) . ?
N1 C14 1.351(3) . ?
N1 C18 1.347(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C17 1.510(4) . ?
N5 H5 0.8800 . ?
N5 C3 1.284(4) . ?
C9 C10 1.390(4) . ?
C9 C2 1.411(4) . ?
C10 H10 0.9500 . ?
C10 C6 1.399(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.385(4) . ?
C11 C14 1.394(4) . ?
C12 H12 0.9500 . ?
C12 C7 1.386(4) . ?
C14 C2 1.475(4) . ?
C18 H18 0.9500 . ?
C18 C7 1.394(4) . ?
C2 C15 1.391(5) . ?
C6 C13 1.394(4) . ?
C6 C8 1.505(4) . ?
C7 H7 0.9500 . ?
C13 H13 0.9500 . ?
C13 C15 1.390(4) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
O2 C3 1.332(3) . ?
O2 C17 1.449(4) . ?
C3 C16 1.504(5) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
F19 C1F 1.329(4) . ?
O1A C1C 1.238(3) . ?
O1B C1C 1.222(4) . ?
C1C C1F 1.562(4) . ?
F1D C1F 1.332(4) . ?
F1E C1F 1.320(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
C4 Au1 N1 172.99(11) . . ?
C4 Au1 N5 89.54(11) . . ?
N5 Au1 N1 97.43(9) . . ?
C9 Au1 N1 80.60(10) . . ?
C9 Au1 C4 92.39(12) . . ?
C9 Au1 N5 174.24(12) . . ?
C14 N1 Au1 113.83(18) . . ?
C18 N1 Au1 125.79(19) . . ?
C18 N1 C14 120.4(2) . . ?
Au1 C4 H4A 109.2 . . ?
Au1 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
C17 C4 Au1 112.18(19) . . ?
C17 C4 H4A 109.2 . . ?
C17 C4 H4B 109.2 . . ?
Au1 N5 H5 117.1 . . ?
C3 N5 Au1 125.7(2) . . ?
C3 N5 H5 117.1 . . ?
C10 C9 Au1 127.2(2) . . ?
C10 C9 C2 119.2(3) . . ?
C2 C9 Au1 113.5(2) . . ?
C9 C10 H10 119.3 . . ?
C9 C10 C6 121.5(3) . . ?
C6 C10 H10 119.3 . . ?
C12 C11 H11 120.1 . . ?
C12 C11 C14 119.8(3) . . ?
C14 C11 H11 120.1 . . ?
C11 C12 H12 120.2 . . ?
C11 C12 C7 119.6(3) . . ?
C7 C12 H12 120.2 . . ?
N1 C14 C11 120.2(3) . . ?
N1 C14 C2 114.5(2) . . ?
C11 C14 C2 125.3(3) . . ?
N1 C18 H18 119.2 . . ?
N1 C18 C7 121.6(3) . . ?
C7 C18 H18 119.2 . . ?
C9 C2 C14 117.3(3) . . ?
C15 C2 C9 119.7(3) . . ?
C15 C2 C14 123.0(2) . . ?
C10 C6 C8 120.5(3) . . ?
C13 C6 C10 118.3(3) . . ?
C13 C6 C8 121.2(3) . . ?
C12 C7 C18 118.4(3) . . ?
C12 C7 H7 120.8 . . ?
C18 C7 H7 120.8 . . ?
C6 C13 H13 119.4 . . ?
C15 C13 C6 121.2(3) . . ?
C15 C13 H13 119.4 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C3 O2 C17 117.0(2) . . ?
N5 C3 O2 122.6(3) . . ?
N5 C3 C16 125.2(3) . . ?
O2 C3 C16 112.2(3) . . ?
C2 C15 H15 120.0 . . ?
C13 C15 C2 120.0(3) . . ?
C13 C15 H15 120.0 . . ?
C3 C16 H16A 109.5 . . ?
C3 C16 H16B 109.5 . . ?
C3 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C4 C17 H17A 108.7 . . ?
C4 C17 H17B 108.7 . . ?
O2 C17 C4 114.4(2) . . ?
O2 C17 H17A 108.7 . . ?
O2 C17 H17B 108.7 . . ?
H17A C17 H17B 107.6 . . ?
O1A C1C C1F 115.0(3) . . ?
O1B C1C O1A 130.2(3) . . ?
O1B C1C C1F 114.8(3) . . ?
F19 C1F C1C 112.9(3) . . ?
F19 C1F F1D 105.6(3) . . ?
F1D C1F C1C 113.2(3) . . ?
F1E C1F F19 106.1(3) . . ?
F1E C1F C1C 111.3(3) . . ?
F1E C1F F1D 107.4(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
Au1 N1 C14 C11 178.4(2) . . . . ?
Au1 N1 C14 C2 -2.9(3) . . . . ?
Au1 N1 C18 C7 179.9(2) . . . . ?
Au1 C4 C17 O2 60.2(3) . . . . ?
Au1 N5 C3 O2 26.5(5) . . . . ?
Au1 N5 C3 C16 -152.2(4) . . . . ?
Au1 C9 C10 C6 178.2(2) . . . . ?
Au1 C9 C2 C14 3.9(4) . . . . ?
Au1 C9 C2 C15 -177.7(3) . . . . ?
N1 C14 C2 C9 -0.5(4) . . . . ?
N1 C14 C2 C15 -178.9(3) . . . . ?
N1 C18 C7 C12 0.7(5) . . . . ?
C9 C10 C6 C13 -1.4(5) . . . . ?
C9 C10 C6 C8 178.3(3) . . . . ?
C9 C2 C15 C13 -0.5(5) . . . . ?
C10 C9 C2 C14 -178.8(3) . . . . ?
C10 C9 C2 C15 -0.4(5) . . . . ?
C10 C6 C13 C15 0.5(5) . . . . ?
C11 C12 C7 C18 -1.0(5) . . . . ?
C11 C14 C2 C9 178.1(3) . . . . ?
C11 C14 C2 C15 -0.3(5) . . . . ?
C12 C11 C14 N1 2.4(5) . . . . ?
C12 C11 C14 C2 -176.1(3) . . . . ?
C14 N1 C18 C7 1.2(5) . . . . ?
C14 C11 C12 C7 -0.5(5) . . . . ?
C14 C2 C15 C13 177.9(3) . . . . ?
C18 N1 C14 C11 -2.8(5) . . . . ?
C18 N1 C14 C2 175.9(3) . . . . ?
C2 C9 C10 C6 1.3(5) . . . . ?
C6 C13 C15 C2 0.4(5) . . . . ?
C8 C6 C13 C15 -179.1(3) . . . . ?
C3 O2 C17 C4 -70.8(4) . . . . ?
C17 O2 C3 N5 21.8(5) . . . . ?
C17 O2 C3 C16 -159.4(3) . . . . ?
O1A C1C C1F F19 132.7(3) . . . . ?
O1A C1C C1F F1D 12.9(5) . . . . ?
O1A C1C C1F F1E -108.2(4) . . . . ?
O1B C1C C1F F19 -46.5(4) . . . . ?
O1B C1C C1F F1D -166.3(3) . . . . ?
O1B C1C C1F F1E 72.6(4) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.5112(6)
2 0.4888(6)

