# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2167546'
loop_
_audit_author_name
_audit_author_address
'Magda Monari'
;University of Bologna
Italy
;
_audit_update_record             
;
2022-04-19 deposited with the CCDC.	2022-06-28 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         ?
_chemical_formula_sum            'C27 H31 Au Cl N3'
_chemical_formula_weight         629.96

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'

_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                   10.6885(8)
_cell_length_b                   16.1197(13)
_cell_length_c                   15.1271(13)
_cell_angle_alpha                90
_cell_angle_beta                 92.152(2)
_cell_angle_gamma                90
_cell_volume                     2604.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9934
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      30.55

_exptl_crystal_description       Prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.607
_exptl_crystal_F_000             1240
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    5.770
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6134
_exptl_absorpt_correction_T_max  0.7941
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31627
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_av_R_equivalents  0.0784
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.847
_diffrn_reflns_theta_max         25.496
_diffrn_reflns_theta_full        25.242
_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             4835
_reflns_number_gt                4047
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0660P)²+12.5610P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4835
_refine_ls_number_parameters     295
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0487
_refine_ls_wR_factor_ref         0.1211
_refine_ls_wR_factor_gt          0.1150
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_restrained_S_all      0.971
_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 0.74244(3) 0.66091(2) 0.40331(2) 0.03986(13) Uani 1 1 d . . . . .
Cl1 Cl 0.8707(3) 0.63779(17) 0.28924(17) 0.0742(8) Uani 1 1 d . . . . .
N2 N 0.6231(5) 0.6441(4) 0.5829(4) 0.0365(14) Uani 1 1 d . . . . .
N1 N 0.5797(6) 0.7595(4) 0.5183(4) 0.0382(14) Uani 1 1 d . . . . .
C1 C 0.6386(6) 0.6862(4) 0.5057(4) 0.0325(15) Uani 1 1 d . . . . .
C8 C 0.7263(6) 0.5105(4) 0.5439(5) 0.0350(15) Uani 1 1 d . . . . .
N3 N 0.8994(7) 0.3387(5) 0.3778(6) 0.064(2) Uani 1 1 d . . . . .
C9 C 0.6705(7) 0.4863(5) 0.4637(5) 0.0423(18) Uani 1 1 d . . . . .
H9 H 0.593656 0.509132 0.446057 0.051 Uiso 1 1 calc R U . . .
C13 C 0.8417(7) 0.4745(5) 0.5665(5) 0.0445(18) Uani 1 1 d . . . . .
H13 H 0.881371 0.488844 0.620052 0.053 Uiso 1 1 calc R U . . .
C3 C 0.5560(7) 0.6935(5) 0.6428(5) 0.0412(17) Uani 1 1 d . . . . .
C4 C 0.5330(8) 0.6630(5) 0.7275(5) 0.049(2) Uani 1 1 d . . . . .
H4 H 0.488376 0.694705 0.766855 0.059 Uiso 1 1 calc R U . . .
C11 C 0.8422(7) 0.3931(5) 0.4327(5) 0.0410(17) Uani 1 1 d . . . . .
C6 C 0.6405(8) 0.5391(5) 0.6894(5) 0.049(2) Uani 1 1 d . . . . .
H6 H 0.667836 0.486646 0.707155 0.058 Uiso 1 1 calc R U . . .
C2 C 0.5290(7) 0.7647(5) 0.5996(5) 0.0422(17) Uani 1 1 d . . . . .
H2 H 0.483930 0.809198 0.621185 0.051 Uiso 1 1 calc R U . . .
C7 C 0.6649(6) 0.5639(5) 0.6069(5) 0.0367(16) Uani 1 1 d . . . . .
C12 C 0.8986(7) 0.4189(5) 0.5130(5) 0.0442(18) Uani 1 1 d . . . . .
H12 H 0.976673 0.397660 0.530318 0.053 Uiso 1 1 calc R U . . .
C25 C 0.7755(9) 0.8807(6) 0.5048(6) 0.060(2) Uani 1 1 d . . . . .
H25 H 0.781231 0.824719 0.529905 0.072 Uiso 1 1 calc R U . . .
C10 C 0.7256(7) 0.4297(5) 0.4098(5) 0.0427(18) Uani 1 1 d . . . . .
H10 H 0.684949 0.414937 0.356640 0.051 Uiso 1 1 calc R U . . .
C5 C 0.5759(8) 0.5878(6) 0.7512(6) 0.056(2) Uani 1 1 d . . . . .
H5 H 0.563327 0.567635 0.807821 0.067 Uiso 1 1 calc R U . . .
C22 C 0.3546(8) 0.7582(6) 0.4069(6) 0.056(2) Uani 1 1 d . . . . .
H22 H 0.387589 0.716091 0.448317 0.067 Uiso 1 1 calc R U . . .
C16 C 0.5642(8) 0.8238(5) 0.4517(6) 0.0449(19) Uani 1 1 d . . . . .
C17 C 0.4552(8) 0.8233(5) 0.3983(6) 0.050(2) Uani 1 1 d . . . . .
C21 C 0.6583(8) 0.8839(5) 0.4472(6) 0.049(2) Uani 1 1 d . . . . .
C15 C 0.8265(10) 0.2971(7) 0.3085(7) 0.074(3) Uani 1 1 d . . . . .
H15A H 0.746830 0.281364 0.330417 0.111 Uiso 1 1 calc R U . . .
H15B H 0.870384 0.248536 0.290045 0.111 Uiso 1 1 calc R U . . .
H15C H 0.814045 0.333979 0.259099 0.111 Uiso 1 1 calc R U . . .
C24 C 0.2369(9) 0.7944(8) 0.4465(8) 0.078(3) Uani 1 1 d . . . . .
H24A H 0.258881 0.820701 0.501906 0.116 Uiso 1 1 calc R U . . .
H24B H 0.177871 0.750757 0.456020 0.116 Uiso 1 1 calc R U . . .
H24C H 0.200225 0.834590 0.406512 0.116 Uiso 1 1 calc R U . . .
C20 C 0.6335(10) 0.9455(6) 0.3843(8) 0.069(3) Uani 1 1 d . . . . .
H20 H 0.692658 0.987198 0.377948 0.083 Uiso 1 1 calc R U . . .
C19 C 0.5286(10) 0.9480(6) 0.3324(8) 0.074(3) Uani 1 1 d . . . . .
H19 H 0.516411 0.990978 0.291918 0.088 Uiso 1 1 calc R U . . .
C14 C 1.0174(9) 0.3033(7) 0.4029(8) 0.073(3) Uani 1 1 d . . . . .
H14A H 1.076065 0.346730 0.417406 0.110 Uiso 1 1 calc R U . . .
H14B H 1.047434 0.271075 0.354745 0.110 Uiso 1 1 calc R U . . .
H14C H 1.008188 0.268185 0.453516 0.110 Uiso 1 1 calc R U . . .
C18 C 0.4394(9) 0.8871(6) 0.3390(7) 0.062(3) Uani 1 1 d . . . . .
H18 H 0.367325 0.889147 0.302650 0.075 Uiso 1 1 calc R U . . .
C23 C 0.3243(11) 0.7144(7) 0.3193(9) 0.088(4) Uani 1 1 d . . . . .
H23A H 0.285010 0.752870 0.278569 0.132 Uiso 1 1 calc R U . . .
H23B H 0.268672 0.668864 0.329060 0.132 Uiso 1 1 calc R U . . .
H23C H 0.400252 0.694022 0.295272 0.132 Uiso 1 1 calc R U . . .
C27 C 0.8925(10) 0.8945(10) 0.4531(9) 0.099(4) Uani 1 1 d . . . . .
H27A H 0.891793 0.857740 0.403134 0.149 Uiso 1 1 calc R U . . .
H27B H 0.965149 0.883677 0.490481 0.149 Uiso 1 1 calc R U . . .
H27C H 0.894512 0.950930 0.432782 0.149 Uiso 1 1 calc R U . . .
C26 C 0.7686(14) 0.9404(11) 0.5811(10) 0.126(6) Uani 1 1 d . . . . .
H26A H 0.770642 0.996250 0.559321 0.190 Uiso 1 1 calc R U . . .
H26B H 0.838699 0.931405 0.621591 0.190 Uiso 1 1 calc R U . . .
H26C H 0.692222 0.931432 0.611121 0.190 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(7) . ?
Au1 Cl1 2.275(2) . ?
N2 C1 1.367(9) . ?
N2 C7 1.411(9) . ?
N2 C3 1.420(10) . ?
N1 C1 1.356(9) . ?
N1 C2 1.365(10) . ?
N1 C16 1.451(10) . ?
C8 C9 1.387(10) . ?
C8 C13 1.394(10) . ?
C8 C7 1.459(10) . ?
N3 C11 1.368(10) . ?
N3 C14 1.422(12) . ?
N3 C15 1.447(12) . ?
C9 C10 1.373(11) . ?
C9 H9 0.9300 . ?
C13 C12 1.366(11) . ?
C13 H13 0.9300 . ?
C3 C2 1.347(11) . ?
C3 C4 1.402(11) . ?
C4 C5 1.340(12) . ?
C4 H4 0.9300 . ?
C11 C12 1.398(11) . ?
C11 C10 1.410(10) . ?
C6 C7 1.346(11) . ?
C6 C5 1.420(12) . ?
C6 H6 0.9300 . ?
C2 H2 0.9300 . ?
C12 H12 0.9300 . ?
C25 C21 1.500(13) . ?
C25 C26 1.507(14) . ?
C25 C27 1.516(14) . ?
C25 H25 0.9800 . ?
C10 H10 0.9300 . ?
C5 H5 0.9300 . ?
C22 C17 1.513(12) . ?
C22 C23 1.524(15) . ?
C22 C24 1.529(14) . ?
C22 H22 0.9800 . ?
C16 C17 1.392(12) . ?
C16 C21 1.400(11) . ?
C17 C18 1.371(12) . ?
C21 C20 1.395(13) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C20 C19 1.346(15) . ?
C20 H20 0.9300 . ?
C19 C18 1.375(14) . ?
C19 H19 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C18 H18 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?

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 176.4(2) . . ?
C1 N2 C7 128.9(6) . . ?
C1 N2 C3 110.3(6) . . ?
C7 N2 C3 120.8(6) . . ?
C1 N1 C2 112.5(6) . . ?
C1 N1 C16 124.5(6) . . ?
C2 N1 C16 122.9(6) . . ?
N1 C1 N2 103.9(6) . . ?
N1 C1 Au1 124.5(5) . . ?
N2 C1 Au1 131.0(5) . . ?
C9 C8 C13 116.4(7) . . ?
C9 C8 C7 123.2(6) . . ?
C13 C8 C7 120.1(7) . . ?
C11 N3 C14 120.5(8) . . ?
C11 N3 C15 119.7(8) . . ?
C14 N3 C15 117.1(8) . . ?
C10 C9 C8 121.8(7) . . ?
C10 C9 H9 119.1 . . ?
C8 C9 H9 119.1 . . ?
C12 C13 C8 122.5(7) . . ?
C12 C13 H13 118.7 . . ?
C8 C13 H13 118.7 . . ?
C2 C3 C4 134.5(8) . . ?
C2 C3 N2 105.8(7) . . ?
C4 C3 N2 119.8(7) . . ?
C5 C4 C3 119.5(8) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
N3 C11 C12 122.0(7) . . ?
N3 C11 C10 122.0(7) . . ?
C12 C11 C10 116.0(7) . . ?
C7 C6 C5 124.2(8) . . ?
C7 C6 H6 117.9 . . ?
C5 C6 H6 117.9 . . ?
C3 C2 N1 107.5(7) . . ?
C3 C2 H2 126.3 . . ?
N1 C2 H2 126.3 . . ?
C6 C7 N2 116.2(7) . . ?
C6 C7 C8 122.6(7) . . ?
N2 C7 C8 121.2(6) . . ?
C13 C12 C11 121.4(7) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C21 C25 C26 111.1(9) . . ?
C21 C25 C27 112.5(9) . . ?
C26 C25 C27 111.5(10) . . ?
C21 C25 H25 107.2 . . ?
C26 C25 H25 107.2 . . ?
C27 C25 H25 107.2 . . ?
C9 C10 C11 121.8(7) . . ?
C9 C10 H10 119.1 . . ?
C11 C10 H10 119.1 . . ?
C4 C5 C6 119.6(8) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C17 C22 C23 112.0(8) . . ?
C17 C22 C24 111.5(8) . . ?
C23 C22 C24 111.5(9) . . ?
C17 C22 H22 107.2 . . ?
C23 C22 H22 107.2 . . ?
C24 C22 H22 107.2 . . ?
C17 C16 C21 124.3(8) . . ?
C17 C16 N1 118.1(7) . . ?
C21 C16 N1 117.6(8) . . ?
C18 C17 C16 117.1(8) . . ?
C18 C17 C22 120.4(8) . . ?
C16 C17 C22 122.4(7) . . ?
C16 C21 C20 114.0(9) . . ?
C16 C21 C25 122.3(8) . . ?
C20 C21 C25 123.6(8) . . ?
N3 C15 H15A 109.5 . . ?
N3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C19 C20 C21 123.6(9) . . ?
C19 C20 H20 118.2 . . ?
C21 C20 H20 118.2 . . ?
C20 C19 C18 120.1(9) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
N3 C14 H14A 109.5 . . ?
N3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C19 C18 C17 121.0(9) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C2 H2 Cl1 0.93 2.98 3.732(8) 138.8 4_576 yes

_refine_diff_density_max         2.299
_refine_diff_density_min         -1.801
_refine_diff_density_rms         0.158



####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2167548'
loop_
_audit_author_name
_audit_author_address
'Magda Monari'
;University of Bologna
Italy
;
_audit_update_record             
;
2022-04-19 deposited with the CCDC.	2022-06-28 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         ?
_chemical_formula_sum            'C21 H27 Au Cl N3'
_chemical_formula_weight         553.87

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'

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

_cell_length_a                   8.1502(11)
_cell_length_b                   15.359(2)
_cell_length_c                   17.032(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2132.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9986
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      28.57

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.726
_exptl_crystal_F_000             1080
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    7.035
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6391
_exptl_absorpt_correction_T_max  0.9014
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20519
_diffrn_reflns_av_unetI/netI     0.0553
_diffrn_reflns_av_R_equivalents  0.0843
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.785
_diffrn_reflns_theta_max         25.496
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3966
_reflns_number_gt                3644
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.744
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0424P)²+1.1572P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.06(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3966
_refine_ls_number_parameters     242
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.0925
_refine_ls_wR_factor_gt          0.0901
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_restrained_S_all      1.117
_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 0.57315(7) 0.38311(3) 0.33979(2) 0.03743(16) Uani 1 1 d . . . . .
Cl1 Cl 0.7393(6) 0.4883(2) 0.3875(2) 0.0642(12) Uani 1 1 d . . . . .
N1 N 0.4637(13) 0.2504(6) 0.2265(5) 0.035(3) Uani 1 1 d . . . . .
N2 N 0.3496(11) 0.2254(5) 0.3375(6) 0.0300(19) Uani 1 1 d . . . . .
N3 N 0.3026(15) 0.3091(7) 0.4505(5) 0.044(3) Uani 1 1 d . . . . .
C1 C 0.4405(17) 0.2847(6) 0.2996(6) 0.032(2) Uani 1 1 d . . . . .
C2 C 0.3886(15) 0.1707(7) 0.2210(7) 0.035(3) Uani 1 1 d . . . . .
H2 H 0.385615 0.135558 0.176518 0.042 Uiso 1 1 calc R U . . .
C3 C 0.3209(15) 0.1521(7) 0.2899(6) 0.032(3) Uani 1 1 d . . . . .
C4 C 0.2422(18) 0.0783(8) 0.3217(7) 0.045(3) Uani 1 1 d . . . . .
H4 H 0.222090 0.029260 0.291184 0.054 Uiso 1 1 calc R U . . .
C5 C 0.197(2) 0.0813(9) 0.3983(8) 0.052(4) Uani 1 1 d . . . . .
H5 H 0.153281 0.031805 0.421884 0.062 Uiso 1 1 calc R U . . .
C6 C 0.2143(19) 0.1573(8) 0.4422(8) 0.049(3) Uani 1 1 d . . . . .
H6 H 0.176365 0.157697 0.493660 0.059 Uiso 1 1 calc R U . . .
C7 C 0.2834(18) 0.2299(8) 0.4136(7) 0.039(3) Uani 1 1 d . . . . .
C8 C 0.200(2) 0.3778(10) 0.4195(8) 0.063(4) Uani 1 1 d . . . . .
H8A H 0.216980 0.382333 0.363855 0.095 Uiso 1 1 calc R U . . .
H8B H 0.229046 0.431939 0.444089 0.095 Uiso 1 1 calc R U . . .
H8C H 0.087303 0.364745 0.429959 0.095 Uiso 1 1 calc R U . . .
C9 C 0.285(3) 0.3045(11) 0.5375(8) 0.072(5) Uani 1 1 d . . . . .
H9A H 0.176243 0.284553 0.550436 0.109 Uiso 1 1 calc R U . . .
H9B H 0.301792 0.361196 0.559691 0.109 Uiso 1 1 calc R U . . .
H9C H 0.364152 0.264650 0.558461 0.109 Uiso 1 1 calc R U . . .
C10 C 0.5602(18) 0.2873(7) 0.1645(7) 0.040(3) Uani 1 1 d . . . . .
C11 C 0.4877(15) 0.3487(8) 0.1170(7) 0.035(3) Uani 1 1 d . . . . .
C12 C 0.5821(19) 0.3793(8) 0.0554(7) 0.048(3) Uani 1 1 d . . . . .
H12 H 0.538582 0.420491 0.021219 0.057 Uiso 1 1 calc R U . . .
C13 C 0.739(2) 0.3497(8) 0.0439(7) 0.057(4) Uani 1 1 d . . . . .
H13 H 0.799636 0.370857 0.001772 0.069 Uiso 1 1 calc R U . . .
C14 C 0.807(2) 0.2902(9) 0.0925(8) 0.052(4) Uani 1 1 d . . . . .
H14 H 0.913800 0.271231 0.083377 0.063 Uiso 1 1 calc R U . . .
C15 C 0.7198(15) 0.2569(7) 0.1563(8) 0.038(3) Uani 1 1 d . . . . .
C16 C 0.3234(19) 0.3850(9) 0.1296(8) 0.060(4) Uani 1 1 d . . . . .
H16 H 0.268206 0.347993 0.168332 0.071 Uiso 1 1 calc R U . . .
C17 C 0.330(2) 0.4762(11) 0.1635(13) 0.086(6) Uani 1 1 d . . . . .
H17A H 0.394585 0.475773 0.210738 0.130 Uiso 1 1 calc R U . . .
H17B H 0.221094 0.495671 0.175274 0.130 Uiso 1 1 calc R U . . .
H17C H 0.379505 0.514829 0.126007 0.130 Uiso 1 1 calc R U . . .
C18 C 0.217(2) 0.3864(13) 0.0565(10) 0.076(5) Uani 1 1 d . . . . .
H18A H 0.263292 0.425581 0.018618 0.115 Uiso 1 1 calc R U . . .
H18B H 0.108294 0.405515 0.070031 0.115 Uiso 1 1 calc R U . . .
H18C H 0.211386 0.328887 0.034487 0.115 Uiso 1 1 calc R U . . .
C19 C 0.801(2) 0.1953(10) 0.2128(8) 0.056(4) Uani 1 1 d . . . . .
H19 H 0.717386 0.176627 0.250626 0.067 Uiso 1 1 calc R U . . .
C20 C 0.935(2) 0.2435(12) 0.2589(9) 0.079(5) Uani 1 1 d . . . . .
H20A H 1.028210 0.252969 0.225495 0.119 Uiso 1 1 calc R U . . .
H20B H 0.967345 0.209137 0.303349 0.119 Uiso 1 1 calc R U . . .
H20C H 0.893300 0.298557 0.276623 0.119 Uiso 1 1 calc R U . . .
C21 C 0.865(3) 0.1161(11) 0.1740(11) 0.103(7) Uani 1 1 d . . . . .
H21A H 0.784324 0.093562 0.138546 0.155 Uiso 1 1 calc R U . . .
H21B H 0.890569 0.073047 0.213010 0.155 Uiso 1 1 calc R U . . .
H21C H 0.963083 0.130494 0.145304 0.155 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 1.980(12) . ?
Au1 Cl1 2.259(3) . ?
N1 C1 1.366(13) . ?
N1 C2 1.372(14) . ?
N1 C10 1.434(15) . ?
N2 C1 1.339(14) . ?
N2 C3 1.406(14) . ?
N2 C7 1.406(15) . ?
N3 C7 1.378(16) . ?
N3 C8 1.444(18) . ?
N3 C9 1.491(16) . ?
C2 C3 1.328(16) . ?
C2 H2 0.9300 . ?
C3 C4 1.410(16) . ?
C4 C5 1.357(19) . ?
C4 H4 0.9300 . ?
C5 C6 1.394(19) . ?
C5 H5 0.9300 . ?
C6 C7 1.340(18) . ?
C6 H6 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.376(17) . ?
C10 C15 1.389(18) . ?
C11 C12 1.384(17) . ?
C11 C16 1.466(19) . ?
C12 C13 1.37(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.35(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.396(19) . ?
C14 H14 0.9300 . ?
C15 C19 1.503(17) . ?
C16 C18 1.52(2) . ?
C16 C17 1.52(2) . ?
C16 H16 0.9800 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C21 1.48(2) . ?
C19 C20 1.54(2) . ?
C19 H19 0.9800 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

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 175.8(4) . . ?
C1 N1 C2 110.2(9) . . ?
C1 N1 C10 126.5(9) . . ?
C2 N1 C10 123.2(9) . . ?
C1 N2 C3 111.1(9) . . ?
C1 N2 C7 128.5(10) . . ?
C3 N2 C7 120.4(9) . . ?
C7 N3 C8 114.4(11) . . ?
C7 N3 C9 113.6(11) . . ?
C8 N3 C9 110.0(12) . . ?
N2 C1 N1 104.7(9) . . ?
N2 C1 Au1 130.9(8) . . ?
N1 C1 Au1 122.3(8) . . ?
C3 C2 N1 108.5(10) . . ?
C3 C2 H2 125.8 . . ?
N1 C2 H2 125.8 . . ?
C2 C3 N2 105.6(9) . . ?
C2 C3 C4 134.5(11) . . ?
N2 C3 C4 119.9(10) . . ?
C5 C4 C3 117.8(12) . . ?
C5 C4 H4 121.1 . . ?
C3 C4 H4 121.1 . . ?
C4 C5 C6 121.0(12) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C7 C6 C5 123.0(12) . . ?
C7 C6 H6 118.5 . . ?
C5 C6 H6 118.5 . . ?
C6 C7 N3 128.0(12) . . ?
C6 C7 N2 117.1(11) . . ?
N3 C7 N2 114.8(10) . . ?
N3 C8 H8A 109.5 . . ?
N3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N3 C9 H9A 109.5 . . ?
N3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C15 125.0(12) . . ?
C11 C10 N1 117.9(12) . . ?
C15 C10 N1 117.1(11) . . ?
C10 C11 C12 116.0(12) . . ?
C10 C11 C16 124.5(11) . . ?
C12 C11 C16 119.4(11) . . ?
C13 C12 C11 121.0(12) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C14 C13 C12 121.3(13) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C13 C14 C15 121.0(15) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C10 C15 C14 115.6(12) . . ?
C10 C15 C19 124.0(12) . . ?
C14 C15 C19 120.3(12) . . ?
C11 C16 C18 114.0(13) . . ?
C11 C16 C17 111.9(14) . . ?
C18 C16 C17 108.7(13) . . ?
C11 C16 H16 107.3 . . ?
C18 C16 H16 107.3 . . ?
C17 C16 H16 107.3 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C21 C19 C15 112.8(12) . . ?
C21 C19 C20 111.8(16) . . ?
C15 C19 C20 109.7(12) . . ?
C21 C19 H19 107.4 . . ?
C15 C19 H19 107.4 . . ?
C20 C19 H19 107.4 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

_refine_diff_density_max         2.100
_refine_diff_density_min         -0.846
_refine_diff_density_rms         0.155



####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2167549'
loop_
_audit_author_name
_audit_author_address
'Magda Monari'
;University of Bologna
Italy
;
_audit_update_record             
;
2022-04-19 deposited with the CCDC.	2022-06-28 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         ?
_chemical_formula_sum            'C28 H40 Au Cl N2 O2'
_chemical_formula_weight         669.03

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                   8.9407(5)
_cell_length_b                   9.6395(6)
_cell_length_c                   17.2392(10)
_cell_angle_alpha                98.233(2)
_cell_angle_beta                 94.272(2)
_cell_angle_gamma                106.185(2)
_cell_volume                     1401.88(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9903
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      30.59

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.585
_exptl_crystal_F_000             668
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    5.368
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3461
_exptl_absorpt_correction_T_max  0.7410
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16780
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.348
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_full        25.242
_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             5216
_reflns_number_gt                5086
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0089P)²+2.2605P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5216
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0226
_refine_ls_R_factor_gt           0.0217
_refine_ls_wR_factor_ref         0.0495
_refine_ls_wR_factor_gt          0.0492
_refine_ls_goodness_of_fit_ref   1.180
_refine_ls_restrained_S_all      1.180
_refine_ls_shift/su_max          0.004
_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
Au Au 0.55354(2) 0.54625(2) 0.23049(2) 0.01654(5) Uani 1 1 d . . . . .
Cl Cl 0.47208(10) 0.75106(9) 0.23663(5) 0.02431(17) Uani 1 1 d . . . . .
O1 O 0.8611(3) 0.6052(3) 0.45322(13) 0.0249(5) Uani 1 1 d . . . . .
H1 H 0.813760 0.664754 0.466303 0.037 Uiso 1 1 calc R U . . .
N1 N 0.5483(3) 0.2401(3) 0.17557(15) 0.0187(5) Uani 1 1 d . . . . .
N2 N 0.7116(3) 0.3222(3) 0.28132(15) 0.0177(5) Uani 1 1 d . . . . .
C1 C 0.6165(4) 0.3637(3) 0.22858(18) 0.0167(6) Uani 1 1 d . . . . .
C18 C 0.5178(4) 0.2474(4) 0.03504(19) 0.0214(7) Uani 1 1 d . . . . .
C14 C 0.2867(4) 0.2014(4) 0.1075(2) 0.0228(7) Uani 1 1 d . . . . .
C13 C 0.4476(4) 0.2317(3) 0.10423(19) 0.0198(7) Uani 1 1 d . . . . .
C17 C 0.4190(4) 0.2296(4) -0.0340(2) 0.0256(7) Uani 1 1 d . . . . .
H17 H 0.461471 0.240363 -0.081215 0.031 Uiso 1 1 calc R U . . .
C16 C 0.2579(5) 0.1959(4) -0.0336(2) 0.0299(8) Uani 1 1 d . . . . .
H16 H 0.193359 0.182179 -0.080664 0.036 Uiso 1 1 calc R U . . .
C8 C 0.8434(4) 0.5688(4) 0.36952(18) 0.0196(7) Uani 1 1 d . . . . .
H8 H 0.751149 0.593532 0.348301 0.024 Uiso 1 1 calc R U . . .
C7 C 0.8137(3) 0.4048(4) 0.34864(18) 0.0182(6) Uani 1 1 d . . . . .
C15 C 0.1924(4) 0.1824(4) 0.0358(2) 0.0283(8) Uani 1 1 d . . . . .
H15 H 0.084124 0.160507 0.035123 0.034 Uiso 1 1 calc R U . . .
C22 C 0.6940(4) 0.2901(4) 0.0345(2) 0.0254(7) Uani 1 1 d . . . . .
H22 H 0.740794 0.276155 0.084969 0.031 Uiso 1 1 calc R U . . .
C19 C 0.2131(4) 0.1886(4) 0.1837(2) 0.0270(8) Uani 1 1 d . . . . .
H19 H 0.298568 0.215836 0.227164 0.032 Uiso 1 1 calc R U . . .
C2 C 0.5930(4) 0.1220(4) 0.1933(2) 0.0221(7) Uani 1 1 d . . . . .
H2 H 0.559650 0.027105 0.164743 0.026 Uiso 1 1 calc R U . . .
C3 C 0.6950(4) 0.1702(4) 0.26032(19) 0.0207(7) Uani 1 1 d . . . . .
C11 C 1.1407(4) 0.6357(5) 0.3731(2) 0.0340(9) Uani 1 1 d . . . . .
H11A H 1.139986 0.536737 0.354350 0.051 Uiso 1 1 calc R U . . .
H11B H 1.146145 0.651712 0.429595 0.051 Uiso 1 1 calc R U . . .
H11C H 1.230117 0.702543 0.357483 0.051 Uiso 1 1 calc R U . . .
C6 C 0.8849(4) 0.3318(4) 0.3937(2) 0.0231(7) Uani 1 1 d . . . . .
H6 H 0.950709 0.384531 0.438981 0.028 Uiso 1 1 calc R U . . .
C21 C 0.1156(5) 0.2948(5) 0.1980(3) 0.0452(11) Uani 1 1 d . . . . .
H21A H 0.179004 0.392429 0.196119 0.068 Uiso 1 1 calc R U . . .
H21B H 0.079434 0.291716 0.248973 0.068 Uiso 1 1 calc R U . . .
H21C H 0.027180 0.267241 0.157987 0.068 Uiso 1 1 calc R U . . .
C12 C 0.9764(4) 0.6250(4) 0.2475(2) 0.0306(8) Uani 1 1 d . . . . .
H12A H 1.071197 0.678589 0.229569 0.046 Uiso 1 1 calc R U . . .
H12B H 0.889350 0.651969 0.224862 0.046 Uiso 1 1 calc R U . . .
H12C H 0.959875 0.521762 0.231499 0.046 Uiso 1 1 calc R U . . .
C9 C 0.9902(4) 0.6611(4) 0.3376(2) 0.0245(7) Uani 1 1 d . . . . .
C4 C 0.7721(4) 0.0991(4) 0.3091(2) 0.0258(7) Uani 1 1 d . . . . .
H4 H 0.759783 -0.000764 0.295976 0.031 Uiso 1 1 calc R U . . .
C10 C 0.9996(5) 0.8224(4) 0.3621(3) 0.0394(9) Uani 1 1 d . . . . .
H10A H 1.086644 0.882655 0.341225 0.059 Uiso 1 1 calc R U . . .
H10B H 1.013951 0.846959 0.418632 0.059 Uiso 1 1 calc R U . . .
H10C H 0.904232 0.838744 0.341763 0.059 Uiso 1 1 calc R U . . .
C24 C 0.7443(5) 0.1960(5) -0.0313(2) 0.0360(9) Uani 1 1 d . . . . .
H24A H 0.702250 0.094437 -0.027492 0.054 Uiso 1 1 calc R U . . .
H24B H 0.856736 0.221712 -0.026341 0.054 Uiso 1 1 calc R U . . .
H24C H 0.705625 0.212691 -0.081538 0.054 Uiso 1 1 calc R U . . .
C5 C 0.8640(4) 0.1788(4) 0.3752(2) 0.0273(8) Uani 1 1 d . . . . .
H5 H 0.913771 0.133348 0.408692 0.033 Uiso 1 1 calc R U . . .
C23 C 0.7550(5) 0.4515(5) 0.0288(3) 0.0442(10) Uani 1 1 d . . . . .
H23A H 0.713355 0.467503 -0.021008 0.066 Uiso 1 1 calc R U . . .
H23B H 0.867434 0.480089 0.032818 0.066 Uiso 1 1 calc R U . . .
H23C H 0.722648 0.508776 0.070911 0.066 Uiso 1 1 calc R U . . .
C20 C 0.1164(6) 0.0318(5) 0.1849(3) 0.0505(12) Uani 1 1 d . . . . .
H20A H 0.034424 0.000270 0.141315 0.076 Uiso 1 1 calc R U . . .
H20B H 0.071006 0.027306 0.233514 0.076 Uiso 1 1 calc R U . . .
H20C H 0.182807 -0.031255 0.180448 0.076 Uiso 1 1 calc R U . . .
O1SB O 0.7510(7) 0.8215(6) 0.5147(3) 0.0384(16) Uani 0.489(5) 1 d . . P A 2
C4SB C 0.7205(11) 0.8014(10) 0.5929(5) 0.037(2) Uani 0.489(5) 1 d . . P A 2
H4S1 H 0.810715 0.855208 0.630951 0.044 Uiso 0.489(5) 1 calc R U P A 2
H4S2 H 0.693113 0.698453 0.597487 0.044 Uiso 0.489(5) 1 calc R U P A 2
C1SB C 0.613(2) 0.842(2) 0.4740(8) 0.085(6) Uani 0.489(5) 1 d . . P A 2
H1S1 H 0.576566 0.769414 0.426359 0.103 Uiso 0.489(5) 1 calc R U P A 2
H1S2 H 0.638850 0.938651 0.459184 0.103 Uiso 0.489(5) 1 calc R U P A 2
C3SB C 0.5833(13) 0.862(2) 0.6049(7) 0.068(4) Uani 0.489(5) 1 d . . P A 2
H3S1 H 0.522003 0.816042 0.643507 0.082 Uiso 0.489(5) 1 calc R U P A 2
H3S2 H 0.619674 0.966981 0.623098 0.082 Uiso 0.489(5) 1 calc R U P A 2
C2SB C 0.4895(14) 0.8272(14) 0.5274(7) 0.049(3) Uani 0.489(5) 1 d . . P A 2
H2S1 H 0.418342 0.728391 0.518068 0.059 Uiso 0.489(5) 1 calc R U P A 2
H2S2 H 0.430069 0.896151 0.521831 0.059 Uiso 0.489(5) 1 calc R U P A 2
O1S O 0.5877(6) 0.5661(6) 0.5103(3) 0.0357(14) Uani 0.511(5) 1 d . . P A 1
C1S C 0.4813(9) 0.6217(9) 0.4676(5) 0.0377(19) Uani 0.511(5) 1 d . . P A 1
H1S3 H 0.374719 0.579424 0.478465 0.045 Uiso 0.511(5) 1 calc R U P A 1
H1S4 H 0.485567 0.599798 0.411284 0.045 Uiso 0.511(5) 1 calc R U P A 1
C4S C 0.6192(12) 0.6490(14) 0.5881(5) 0.061(3) Uani 0.511(5) 1 d . . P A 1
H4S3 H 0.724050 0.656617 0.611193 0.074 Uiso 0.511(5) 1 calc R U P A 1
H4S4 H 0.544497 0.602279 0.621329 0.074 Uiso 0.511(5) 1 calc R U P A 1
C3S C 0.6051(18) 0.7949(14) 0.5813(9) 0.077(4) Uani 0.511(5) 1 d . . P A 1
H3S3 H 0.707195 0.867688 0.592436 0.093 Uiso 0.511(5) 1 calc R U P A 1
H3S4 H 0.537107 0.822308 0.618100 0.093 Uiso 0.511(5) 1 calc R U P A 1
C2S C 0.5351(16) 0.7843(14) 0.4965(9) 0.057(3) Uani 0.511(5) 1 d . . P A 1
H2S3 H 0.447781 0.825522 0.494625 0.068 Uiso 0.511(5) 1 calc R U P A 1
H2S4 H 0.613240 0.833794 0.465631 0.068 Uiso 0.511(5) 1 calc R U P A 1


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Au C1 1.988(3) . ?
Au Cl 2.2787(8) . ?
O1 C8 1.421(4) . ?
O1 H1 0.8200 . ?
N1 C1 1.352(4) . ?
N1 C2 1.372(4) . ?
N1 C13 1.448(4) . ?
N2 C1 1.374(4) . ?
N2 C7 1.410(4) . ?
N2 C3 1.421(4) . ?
C18 C17 1.389(5) . ?
C18 C13 1.396(5) . ?
C18 C22 1.514(5) . ?
C14 C13 1.393(5) . ?
C14 C15 1.402(5) . ?
C14 C19 1.519(5) . ?
C17 C16 1.386(5) . ?
C17 H17 0.9300 . ?
C16 C15 1.378(5) . ?
C16 H16 0.9300 . ?
C8 C7 1.512(5) . ?
C8 C9 1.554(5) . ?
C8 H8 0.9800 . ?
C7 C6 1.356(5) . ?
C15 H15 0.9300 . ?
C22 C23 1.519(5) . ?
C22 C24 1.523(5) . ?
C22 H22 0.9800 . ?
C19 C20 1.521(6) . ?
C19 C21 1.525(5) . ?
C19 H19 0.9800 . ?
C2 C3 1.355(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.413(5) . ?
C11 C9 1.533(5) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C6 C5 1.420(5) . ?
C6 H6 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C12 C9 1.530(5) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C9 C10 1.528(5) . ?
C4 C5 1.349(5) . ?
C4 H4 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C5 H5 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
O1SB C4SB 1.425(10) . ?
O1SB C1SB 1.447(15) . ?
C4SB C3SB 1.513(14) . ?
C4SB H4S1 0.9700 . ?
C4SB H4S2 0.9700 . ?
C1SB C2SB 1.481(17) . ?
C1SB H1S1 0.9700 . ?
C1SB H1S2 0.9700 . ?
C3SB C2SB 1.466(17) . ?
C3SB H3S1 0.9700 . ?
C3SB H3S2 0.9700 . ?
C2SB H2S1 0.9700 . ?
C2SB H2S2 0.9700 . ?
O1S C4S 1.424(11) . ?
O1S C1S 1.423(9) . ?
O1S O1S 1.698(11) 2_666 ?
O1S C1S 1.847(10) 2_666 ?
C1S C2S 1.502(15) . ?
C1S H1S3 0.9700 . ?
C1S H1S4 0.9700 . ?
C4S C3S 1.466(18) . ?
C4S H4S3 0.9700 . ?
C4S H4S4 0.9700 . ?
C3S C2S 1.52(2) . ?
C3S H3S3 0.9700 . ?
C3S H3S4 0.9700 . ?
C2S H2S3 0.9700 . ?
C2S H2S4 0.9700 . ?

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 Au Cl 177.13(9) . . ?
C8 O1 H1 109.5 . . ?
C1 N1 C2 112.7(3) . . ?
C1 N1 C13 124.9(3) . . ?
C2 N1 C13 122.2(3) . . ?
C1 N2 C7 130.3(3) . . ?
C1 N2 C3 109.9(3) . . ?
C7 N2 C3 119.8(3) . . ?
N1 C1 N2 104.2(3) . . ?
N1 C1 Au 123.2(2) . . ?
N2 C1 Au 131.9(2) . . ?
C17 C18 C13 117.0(3) . . ?
C17 C18 C22 120.5(3) . . ?
C13 C18 C22 122.5(3) . . ?
C13 C14 C15 116.7(3) . . ?
C13 C14 C19 123.0(3) . . ?
C15 C14 C19 120.3(3) . . ?
C14 C13 C18 123.9(3) . . ?
C14 C13 N1 118.6(3) . . ?
C18 C13 N1 117.5(3) . . ?
C16 C17 C18 120.9(3) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 H17 119.5 . . ?
C15 C16 C17 120.6(3) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
O1 C8 C7 107.4(3) . . ?
O1 C8 C9 109.4(3) . . ?
C7 C8 C9 114.3(3) . . ?
O1 C8 H8 108.5 . . ?
C7 C8 H8 108.5 . . ?
C9 C8 H8 108.5 . . ?
C6 C7 N2 117.4(3) . . ?
C6 C7 C8 121.3(3) . . ?
N2 C7 C8 121.3(3) . . ?
C16 C15 C14 120.9(3) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C18 C22 C23 109.7(3) . . ?
C18 C22 C24 112.7(3) . . ?
C23 C22 C24 110.8(3) . . ?
C18 C22 H22 107.8 . . ?
C23 C22 H22 107.8 . . ?
C24 C22 H22 107.8 . . ?
C14 C19 C20 111.4(3) . . ?
C14 C19 C21 111.2(3) . . ?
C20 C19 C21 111.3(4) . . ?
C14 C19 H19 107.6 . . ?
C20 C19 H19 107.6 . . ?
C21 C19 H19 107.6 . . ?
C3 C2 N1 106.8(3) . . ?
C3 C2 H2 126.6 . . ?
N1 C2 H2 126.6 . . ?
C2 C3 C4 133.1(3) . . ?
C2 C3 N2 106.2(3) . . ?
C4 C3 N2 120.5(3) . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C7 C6 C5 123.3(3) . . ?
C7 C6 H6 118.4 . . ?
C5 C6 H6 118.4 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C9 C12 109.1(3) . . ?
C10 C9 C11 108.8(3) . . ?
C12 C9 C11 109.2(3) . . ?
C10 C9 C8 107.2(3) . . ?
C12 C9 C8 111.2(3) . . ?
C11 C9 C8 111.3(3) . . ?
C5 C4 C3 118.8(3) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C4 C5 C6 120.1(3) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C4SB O1SB C1SB 108.3(7) . . ?
O1SB C4SB C3SB 103.4(8) . . ?
O1SB C4SB H4S1 111.1 . . ?
C3SB C4SB H4S1 111.1 . . ?
O1SB C4SB H4S2 111.1 . . ?
C3SB C4SB H4S2 111.1 . . ?
H4S1 C4SB H4S2 109.0 . . ?
O1SB C1SB C2SB 108.7(9) . . ?
O1SB C1SB H1S1 110.0 . . ?
C2SB C1SB H1S1 110.0 . . ?
O1SB C1SB H1S2 110.0 . . ?
C2SB C1SB H1S2 110.0 . . ?
H1S1 C1SB H1S2 108.3 . . ?
C2SB C3SB C4SB 105.4(10) . . ?
C2SB C3SB H3S1 110.7 . . ?
C4SB C3SB H3S1 110.7 . . ?
C2SB C3SB H3S2 110.7 . . ?
C4SB C3SB H3S2 110.7 . . ?
H3S1 C3SB H3S2 108.8 . . ?
C1SB C2SB C3SB 101.3(10) . . ?
C1SB C2SB H2S1 111.5 . . ?
C3SB C2SB H2S1 111.5 . . ?
C1SB C2SB H2S2 111.5 . . ?
C3SB C2SB H2S2 111.5 . . ?
H2S1 C2SB H2S2 109.3 . . ?
C4S O1S C1S 106.2(6) . . ?
C4S O1S O1S 115.4(7) . 2_666 ?
C1S O1S O1S 71.9(5) . 2_666 ?
C4S O1S C1S 100.4(7) . 2_666 ?
C1S O1S C1S 119.0(5) . 2_666 ?
O1S O1S C1S 47.1(4) 2_666 2_666 ?
O1S C1S C2S 104.9(7) . . ?
O1S C1S O1S 61.0(5) . 2_666 ?
C2S C1S O1S 149.1(9) . 2_666 ?
O1S C1S H1S3 110.8 . . ?
C2S C1S H1S3 110.8 . . ?
O1S C1S H1S3 57.9 2_666 . ?
O1S C1S H1S4 110.8 . . ?
C2S C1S H1S4 110.8 . . ?
O1S C1S H1S4 100.1 2_666 . ?
H1S3 C1S H1S4 108.8 . . ?
O1S C4S C3S 106.9(9) . . ?
O1S C4S H4S3 110.3 . . ?
C3S C4S H4S3 110.3 . . ?
O1S C4S H4S4 110.3 . . ?
C3S C4S H4S4 110.3 . . ?
H4S3 C4S H4S4 108.6 . . ?
C4S C3S C2S 106.1(9) . . ?
C4S C3S H3S3 110.5 . . ?
C2S C3S H3S3 110.5 . . ?
C4S C3S H3S4 110.5 . . ?
C2S C3S H3S4 110.5 . . ?
H3S3 C3S H3S4 108.7 . . ?
C1S C2S C3S 102.3(10) . . ?
C1S C2S H2S3 111.3 . . ?
C3S C2S H2S3 111.3 . . ?
C1S C2S H2S4 111.3 . . ?
C3S C2S H2S4 111.3 . . ?
H2S3 C2S H2S4 109.2 . . ?

_refine_diff_density_max         1.146
_refine_diff_density_min         -1.421
_refine_diff_density_rms         0.094



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 2167547'
loop_
_audit_author_name
_audit_author_address
'Magda Monari'
;University of Bologna
Italy
;
_audit_update_record             
;
2022-04-19 deposited with the CCDC.	2022-06-28 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         ?
_chemical_formula_sum            'C27 H31 Au Br N3'
_chemical_formula_weight         674.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   10.8669(7)
_cell_length_b                   11.9595(8)
_cell_length_c                   19.9146(12)
_cell_angle_alpha                90
_cell_angle_beta                 100.258(2)
_cell_angle_gamma                90
_cell_volume                     2546.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9993
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      28.29

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.759
_exptl_crystal_F_000             1312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_absorpt_coefficient_mu    7.364
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4684
_exptl_absorpt_correction_T_max  0.7311
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32398
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_av_R_equivalents  0.0611
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.904
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_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             5009
_reflns_number_gt                4270
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0559P)²+12.8393P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5009
_refine_ls_number_parameters     295
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_ref         0.1133
_refine_ls_wR_factor_gt          0.1080
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_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
Au Au 0.20501(3) 0.26891(2) 0.46022(2) 0.04250(12) Uani 1 1 d . . . . .
Br Br 0.17036(14) 0.18788(10) 0.34867(5) 0.0910(4) Uani 1 1 d . . . . .
N2 N 0.2570(5) 0.2712(4) 0.6119(3) 0.0367(12) Uani 1 1 d . . . . .
N1 N 0.2156(5) 0.4397(4) 0.5767(3) 0.0329(11) Uani 1 1 d . . . . .
C1 C 0.2321(5) 0.3332(5) 0.5545(3) 0.0280(12) Uani 1 1 d . . . . .
C3 C 0.2243(6) 0.4397(5) 0.6481(3) 0.0350(14) Uani 1 1 d . . . . .
C2 C 0.2535(6) 0.3336(6) 0.6691(3) 0.0380(15) Uani 1 1 d . . . . .
H2 H 0.268390 0.308020 0.713926 0.046 Uiso 1 1 calc R U . . .
C9 C 0.3058(6) 0.5043(5) 0.4449(4) 0.0376(14) Uani 1 1 d . . . . .
H9 H 0.370633 0.474619 0.476729 0.045 Uiso 1 1 calc R U . . .
C7 C 0.1862(6) 0.5376(5) 0.5385(3) 0.0353(14) Uani 1 1 d . . . . .
C8 C 0.1967(6) 0.5405(5) 0.4659(4) 0.0384(15) Uani 1 1 d . . . . .
C21 C 0.1722(6) 0.0848(5) 0.6180(3) 0.0361(14) Uani 1 1 d . . . . .
N3 N 0.4321(6) 0.4783(7) 0.3571(4) 0.0600(18) Uani 1 1 d . . . . .
C16 C 0.2746(6) 0.1512(5) 0.6125(3) 0.0349(14) Uani 1 1 d . . . . .
C10 C 0.3187(6) 0.5122(6) 0.3763(4) 0.0432(16) Uani 1 1 d . . . . .
C13 C 0.1016(6) 0.5856(6) 0.4187(4) 0.0457(17) Uani 1 1 d . . . . .
H13 H 0.029474 0.611803 0.432531 0.055 Uiso 1 1 calc R U . . .
C25 C 0.0451(6) 0.1336(6) 0.6222(4) 0.0448(16) Uani 1 1 d . . . . .
H25 H 0.053384 0.215128 0.620556 0.054 Uiso 1 1 calc R U . . .
C20 C 0.1911(7) -0.0294(6) 0.6192(4) 0.0479(17) Uani 1 1 d . . . . .
H20 H 0.125249 -0.076937 0.623540 0.057 Uiso 1 1 calc R U . . .
C6 C 0.1536(7) 0.6275(6) 0.5717(4) 0.0481(18) Uani 1 1 d . . . . .
H6 H 0.129205 0.691957 0.546742 0.058 Uiso 1 1 calc R U . . .
C17 C 0.3940(7) 0.1091(6) 0.6087(3) 0.0423(16) Uani 1 1 d . . . . .
C4 C 0.1929(7) 0.5388(6) 0.6806(4) 0.0472(17) Uani 1 1 d . . . . .
H4 H 0.199157 0.540830 0.727740 0.057 Uiso 1 1 calc R U . . .
C18 C 0.4065(7) -0.0049(7) 0.6105(4) 0.0507(18) Uani 1 1 d . . . . .
H18 H 0.484176 -0.036666 0.609167 0.061 Uiso 1 1 calc R U . . .
C11 C 0.2209(8) 0.5549(7) 0.3301(4) 0.0517(18) Uani 1 1 d . . . . .
H11 H 0.226958 0.559069 0.284206 0.062 Uiso 1 1 calc R U . . .
C19 C 0.3052(8) -0.0737(6) 0.6143(4) 0.0521(19) Uani 1 1 d . . . . .
H19 H 0.314938 -0.150933 0.613438 0.062 Uiso 1 1 calc R U . . .
C22 C 0.5045(7) 0.1853(7) 0.6044(4) 0.0517(19) Uani 1 1 d . . . . .
H22 H 0.476137 0.262886 0.605778 0.062 Uiso 1 1 calc R U . . .
C5 C 0.1545(8) 0.6288(7) 0.6433(4) 0.055(2) Uani 1 1 d . . . . .
H5 H 0.128488 0.692224 0.663954 0.066 Uiso 1 1 calc R U . . .
C12 C 0.1132(8) 0.5917(7) 0.3515(4) 0.056(2) Uani 1 1 d . . . . .
H12 H 0.047945 0.620915 0.319715 0.067 Uiso 1 1 calc R U . . .
C27 C 0.0058(8) 0.1055(8) 0.6900(5) 0.064(2) Uani 1 1 d . . . . .
H27A H -0.013817 0.027305 0.691104 0.096 Uiso 1 1 calc R U . . .
H27B H -0.066624 0.148699 0.694806 0.096 Uiso 1 1 calc R U . . .
H27C H 0.072921 0.122741 0.726789 0.096 Uiso 1 1 calc R U . . .
C26 C -0.0533(8) 0.1003(9) 0.5617(5) 0.067(2) Uani 1 1 d . . . . .
H26A H -0.021649 0.112718 0.520279 0.101 Uiso 1 1 calc R U . . .
H26B H -0.127121 0.144576 0.561250 0.101 Uiso 1 1 calc R U . . .
H26C H -0.073341 0.022649 0.565263 0.101 Uiso 1 1 calc R U . . .
C14 C 0.4920(8) 0.3806(9) 0.3886(5) 0.074(3) Uani 1 1 d . . . . .
H14A H 0.488125 0.381214 0.436436 0.111 Uiso 1 1 calc R U . . .
H14B H 0.577811 0.379618 0.382888 0.111 Uiso 1 1 calc R U . . .
H14C H 0.450204 0.315235 0.367849 0.111 Uiso 1 1 calc R U . . .
C24 C 0.5519(10) 0.1678(11) 0.5379(6) 0.089(3) Uani 1 1 d . . . . .
H24A H 0.622900 0.215239 0.536973 0.133 Uiso 1 1 calc R U . . .
H24B H 0.486869 0.186105 0.500185 0.133 Uiso 1 1 calc R U . . .
H24C H 0.575985 0.091093 0.534368 0.133 Uiso 1 1 calc R U . . .
C15 C 0.4388(10) 0.4911(12) 0.2857(5) 0.089(4) Uani 1 1 d . . . . .
H15A H 0.383180 0.438732 0.259233 0.134 Uiso 1 1 calc R U . . .
H15B H 0.522820 0.477298 0.278998 0.134 Uiso 1 1 calc R U . . .
H15C H 0.414843 0.565843 0.271294 0.134 Uiso 1 1 calc R U . . .
C23 C 0.6073(9) 0.1670(10) 0.6640(6) 0.083(3) Uani 1 1 d . . . . .
H23A H 0.580656 0.191865 0.704955 0.125 Uiso 1 1 calc R U . . .
H23B H 0.679844 0.208568 0.657500 0.125 Uiso 1 1 calc R U . . .
H23C H 0.627484 0.088851 0.667824 0.125 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
Au C1 2.002(6) . ?
Au Br 2.3913(9) . ?
N2 C1 1.348(8) . ?
N2 C2 1.368(8) . ?
N2 C16 1.447(9) . ?
N1 C1 1.371(8) . ?
N1 C7 1.401(8) . ?
N1 C3 1.408(8) . ?
C3 C2 1.357(10) . ?
C3 C4 1.421(9) . ?
C2 H2 0.9300 . ?
C9 C8 1.394(9) . ?
C9 C10 1.401(10) . ?
C9 H9 0.9300 . ?
C7 C6 1.342(10) . ?
C7 C8 1.472(9) . ?
C8 C13 1.377(10) . ?
C21 C20 1.381(10) . ?
C21 C16 1.386(9) . ?
C21 C25 1.516(9) . ?
N3 C10 1.413(9) . ?
N3 C14 1.428(13) . ?
N3 C15 1.445(11) . ?
C16 C17 1.407(9) . ?
C10 C11 1.374(11) . ?
C13 C12 1.369(11) . ?
C13 H13 0.9300 . ?
C25 C26 1.514(11) . ?
C25 C27 1.525(11) . ?
C25 H25 0.9800 . ?
C20 C19 1.368(11) . ?
C20 H20 0.9300 . ?
C6 C5 1.425(11) . ?
C6 H6 0.9300 . ?
C17 C18 1.370(11) . ?
C17 C22 1.521(10) . ?
C4 C5 1.331(12) . ?
C4 H4 0.9300 . ?
C18 C19 1.388(11) . ?
C18 H18 0.9300 . ?
C11 C12 1.386(11) . ?
C11 H11 0.9300 . ?
C19 H19 0.9300 . ?
C22 C23 1.494(13) . ?
C22 C24 1.520(12) . ?
C22 H22 0.9800 . ?
C5 H5 0.9300 . ?
C12 H12 0.9300 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

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 Au Br 178.51(17) . . ?
C1 N2 C2 112.0(5) . . ?
C1 N2 C16 124.0(5) . . ?
C2 N2 C16 123.8(6) . . ?
C1 N1 C7 129.2(5) . . ?
C1 N1 C3 109.6(5) . . ?
C7 N1 C3 121.0(5) . . ?
N2 C1 N1 104.9(5) . . ?
N2 C1 Au 123.9(4) . . ?
N1 C1 Au 130.8(4) . . ?
C2 C3 N1 106.4(5) . . ?
C2 C3 C4 134.6(7) . . ?
N1 C3 C4 118.8(6) . . ?
C3 C2 N2 107.0(6) . . ?
C3 C2 H2 126.5 . . ?
N2 C2 H2 126.5 . . ?
C8 C9 C10 120.6(6) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C6 C7 N1 117.2(6) . . ?
C6 C7 C8 122.6(6) . . ?
N1 C7 C8 120.2(6) . . ?
C13 C8 C9 119.5(7) . . ?
C13 C8 C7 120.0(6) . . ?
C9 C8 C7 120.4(6) . . ?
C20 C21 C16 116.7(6) . . ?
C20 C21 C25 120.9(6) . . ?
C16 C21 C25 122.4(6) . . ?
C10 N3 C14 117.8(7) . . ?
C10 N3 C15 115.8(7) . . ?
C14 N3 C15 114.9(8) . . ?
C21 C16 C17 124.0(6) . . ?
C21 C16 N2 117.5(6) . . ?
C17 C16 N2 118.5(6) . . ?
C11 C10 C9 118.5(7) . . ?
C11 C10 N3 122.2(7) . . ?
C9 C10 N3 119.2(7) . . ?
C12 C13 C8 120.0(7) . . ?
C12 C13 H13 120.0 . . ?
C8 C13 H13 120.0 . . ?
C21 C25 C26 112.1(7) . . ?
C21 C25 C27 111.5(6) . . ?
C26 C25 C27 112.1(7) . . ?
C21 C25 H25 106.9 . . ?
C26 C25 H25 106.9 . . ?
C27 C25 H25 106.9 . . ?
C19 C20 C21 121.0(7) . . ?
C19 C20 H20 119.5 . . ?
C21 C20 H20 119.5 . . ?
C7 C6 C5 123.1(7) . . ?
C7 C6 H6 118.4 . . ?
C5 C6 H6 118.4 . . ?
C18 C17 C16 116.3(7) . . ?
C18 C17 C22 121.5(7) . . ?
C16 C17 C22 122.2(6) . . ?
C5 C4 C3 119.8(7) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C17 C18 C19 121.0(7) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C10 C11 C12 120.5(7) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C20 C19 C18 120.8(7) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C23 C22 C17 110.8(7) . . ?
C23 C22 C24 110.5(8) . . ?
C17 C22 C24 111.1(8) . . ?
C23 C22 H22 108.1 . . ?
C17 C22 H22 108.1 . . ?
C24 C22 H22 108.1 . . ?
C4 C5 C6 119.6(7) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C13 C12 C11 120.8(7) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N3 C14 H14A 109.5 . . ?
N3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N3 C15 H15A 109.5 . . ?
N3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

_refine_diff_density_max         1.876
_refine_diff_density_min         -1.714
_refine_diff_density_rms         0.143



####################################################################### 
# 
# 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_shelx_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 2167551'
loop_
_audit_author_name
_audit_author_address
'Magda Monari'
;University of Bologna
Italy
;
_audit_update_record             
;
2022-04-19 deposited with the CCDC.	2022-06-28 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         ?
_chemical_formula_sum            'C26 H34 Au Cl N2 O2'
_chemical_formula_weight         638.97

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'
Au Au -2.0133 8.8022 '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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   9.8777(7)
_cell_length_b                   13.2885(10)
_cell_length_c                   19.8719(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2608.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9913
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      28.35


_exptl_crystal_description       Needle
_exptl_crystal_colour            pale-yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.627
_exptl_crystal_F_000             1264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    5.766
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5473
_exptl_absorpt_correction_T_max  0.8124
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30416
_diffrn_reflns_av_unetI/netI     0.0434
_diffrn_reflns_av_R_equivalents  0.0626
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.844
_diffrn_reflns_theta_max         25.248
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             4669
_reflns_number_gt                4549
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.759
_reflns_Friedel_fraction_max     0.984
_reflns_Friedel_fraction_full    0.984

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+117.5266P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_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 1877 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.044(6)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         4669
_refine_ls_number_parameters     297
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0388
_refine_ls_wR_factor_ref         0.1004
_refine_ls_wR_factor_gt          0.0997
_refine_ls_goodness_of_fit_ref   0.766
_refine_ls_restrained_S_all      0.766
_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
Au Au 0.21637(5) 0.15948(4) 0.69590(3) 0.01358(14) Uani 1 1 d . . . . .
C1 C 0.1033(14) 0.2582(10) 0.7462(7) 0.013(3) Uani 1 1 d . . . . .
C21 C -0.1868(19) 0.1725(14) 0.6582(9) 0.037(5) Uani 1 1 d . . . . .
H21 H -0.157136 0.179620 0.704990 0.044 Uiso 1 1 calc R U . . .
C2 C -0.0733(14) 0.3623(10) 0.7614(7) 0.017(3) Uani 1 1 d . . . . .
H2 H -0.147794 0.402766 0.752059 0.021 Uiso 1 1 calc R U . . .
C8 C 0.3096(14) 0.2032(10) 0.8544(6) 0.015(3) Uani 1 1 d . . . . .
H8 H 0.307548 0.167005 0.811413 0.018 Uiso 1 1 calc R U . . .
C15 C -0.0151(14) 0.3145(10) 0.6440(7) 0.017(3) Uani 1 1 d . . . . .
C4 C -0.0646(16) 0.3649(11) 0.8896(8) 0.022(3) Uani 1 1 d . . . . .
H4 H -0.140463 0.404739 0.897243 0.027 Uiso 1 1 calc R U . . .
N2 N 0.0908(11) 0.2783(8) 0.8132(6) 0.014(2) Uani 1 1 d . . . . .
C6 C 0.1282(16) 0.2714(11) 0.9295(7) 0.021(3) Uani 1 1 d . . . . .
H6 H 0.178082 0.248468 0.966076 0.025 Uiso 1 1 calc R U . . .
C9 C 0.4256(16) 0.2793(12) 0.8528(8) 0.022(3) Uani 1 1 d . . . . .
C7 C 0.1716(14) 0.2501(10) 0.8667(7) 0.014(3) Uani 1 1 d . . . . .
C5 C 0.0076(17) 0.3282(13) 0.9413(7) 0.025(4) Uani 1 1 d . . . . .
H5 H -0.021059 0.339797 0.985157 0.030 Uiso 1 1 calc R U . . .
N1 N 0.0054(11) 0.3125(8) 0.7154(5) 0.013(3) Uani 1 1 d . . . . .
C3 C -0.0227(13) 0.3415(13) 0.8225(7) 0.020(3) Uani 1 1 d . . . . .
C16 C -0.1061(14) 0.2462(11) 0.6157(8) 0.018(3) Uani 1 1 d . . . . .
C11 C 0.4316(16) 0.3453(14) 0.9167(7) 0.026(3) Uani 1 1 d . . . . .
H11A H 0.352065 0.386600 0.919036 0.039 Uiso 1 1 calc R U . . .
H11B H 0.510562 0.387334 0.914988 0.039 Uiso 1 1 calc R U . . .
H11C H 0.436022 0.302889 0.955755 0.039 Uiso 1 1 calc R U . . .
C12 C 0.5603(16) 0.2208(13) 0.8472(8) 0.028(4) Uani 1 1 d . . . . .
H12A H 0.573710 0.181364 0.887060 0.042 Uiso 1 1 calc R U . . .
H12B H 0.633735 0.267559 0.842216 0.042 Uiso 1 1 calc R U . . .
H12C H 0.557094 0.177267 0.808652 0.042 Uiso 1 1 calc R U . . .
C17 C -0.1247(17) 0.2498(12) 0.5471(8) 0.027(4) Uani 1 1 d . . . . .
H17 H -0.185716 0.205712 0.526979 0.032 Uiso 1 1 calc R U . . .
C20 C 0.0572(15) 0.3834(12) 0.6060(8) 0.021(3) Uani 1 1 d . . . . .
C10 C 0.4116(14) 0.3472(13) 0.7909(6) 0.023(3) Uani 1 1 d . . . . .
H10A H 0.410228 0.306496 0.751002 0.034 Uiso 1 1 calc R U . . .
H10B H 0.486995 0.392708 0.789000 0.034 Uiso 1 1 calc R U . . .
H10C H 0.328951 0.384869 0.793951 0.034 Uiso 1 1 calc R U . . .
Cl Cl 0.3366(4) 0.0414(3) 0.6393(2) 0.0244(8) Uani 1 1 d . . . . .
O1 O 0.3359(11) 0.1314(7) 0.9084(5) 0.023(2) Uani 1 1 d . . . . .
C13 C 0.3041(16) 0.0345(11) 0.8971(7) 0.022(3) Uani 1 1 d . . . . .
O2 O 0.2528(14) 0.0062(8) 0.8461(6) 0.039(4) Uani 1 1 d . . . . .
C14 C 0.3402(18) -0.0291(13) 0.9560(8) 0.030(4) Uani 1 1 d . . . . .
H14A H 0.278595 -0.015536 0.992258 0.046 Uiso 1 1 calc R U . . .
H14B H 0.430873 -0.013846 0.970059 0.046 Uiso 1 1 calc R U . . .
H14C H 0.334327 -0.098785 0.943709 0.046 Uiso 1 1 calc R U . . .
C19 C 0.0352(18) 0.3836(14) 0.5369(9) 0.031(4) Uani 1 1 d . . . . .
H19 H 0.081793 0.429194 0.509961 0.038 Uiso 1 1 calc R U . . .
C18 C -0.0551(18) 0.3170(14) 0.5077(8) 0.033(4) Uani 1 1 d . . . . .
H18 H -0.068497 0.317774 0.461360 0.039 Uiso 1 1 calc R U . . .
C24 C 0.1566(17) 0.4558(12) 0.6382(9) 0.026(4) Uani 1 1 d . . . . .
H24 H 0.162631 0.438605 0.686063 0.032 Uiso 1 1 calc R U . . .
C26 C 0.2981(19) 0.4450(14) 0.6082(10) 0.041(5) Uani 1 1 d . . . . .
H26A H 0.325570 0.375734 0.610059 0.062 Uiso 1 1 calc R U . . .
H26B H 0.360731 0.485330 0.633446 0.062 Uiso 1 1 calc R U . . .
H26C H 0.297111 0.467108 0.562208 0.062 Uiso 1 1 calc R U . . .
C22 C -0.3370(19) 0.195(2) 0.6555(10) 0.059(8) Uani 1 1 d . . . . .
H22A H -0.364827 0.201995 0.609452 0.089 Uiso 1 1 calc R U . . .
H22B H -0.355400 0.256032 0.679422 0.089 Uiso 1 1 calc R U . . .
H22C H -0.386142 0.140414 0.675901 0.089 Uiso 1 1 calc R U . . .
C25 C 0.107(2) 0.5649(14) 0.6333(13) 0.051(6) Uani 1 1 d . . . . .
H25A H 0.096180 0.582998 0.586787 0.077 Uiso 1 1 calc R U . . .
H25B H 0.171882 0.608835 0.653936 0.077 Uiso 1 1 calc R U . . .
H25C H 0.021515 0.571214 0.655953 0.077 Uiso 1 1 calc R U . . .
C23 C -0.154(3) 0.0654(16) 0.6353(16) 0.077(9) Uani 1 1 d . . . . .
H23A H -0.184608 0.056054 0.589885 0.115 Uiso 1 1 calc R U . . .
H23B H -0.199157 0.018152 0.664241 0.115 Uiso 1 1 calc R U . . .
H23C H -0.058131 0.054665 0.637532 0.115 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
Au C1 1.992(14) . ?
Au Cl 2.267(4) . ?
C1 N1 1.352(18) . ?
C1 N2 1.364(19) . ?
C21 C16 1.52(2) . ?
C21 C22 1.51(3) . ?
C21 C23 1.53(3) . ?
C2 C3 1.34(2) . ?
C2 N1 1.371(18) . ?
C8 O1 1.459(16) . ?
C8 C7 1.519(19) . ?
C8 C9 1.53(2) . ?
C15 C16 1.40(2) . ?
C15 C20 1.38(2) . ?
C15 N1 1.433(19) . ?
C4 C5 1.34(2) . ?
C4 C3 1.43(2) . ?
N2 C7 1.382(18) . ?
N2 C3 1.413(18) . ?
C6 C7 1.35(2) . ?
C6 C5 1.43(2) . ?
C9 C10 1.53(2) . ?
C9 C12 1.54(2) . ?
C9 C11 1.54(2) . ?
C16 C17 1.38(2) . ?
C17 C18 1.37(2) . ?
C20 C19 1.39(2) . ?
C20 C24 1.52(2) . ?
O1 C13 1.345(17) . ?
C13 O2 1.193(18) . ?
C13 C14 1.49(2) . ?
C19 C18 1.38(3) . ?
C24 C26 1.53(2) . ?
C24 C25 1.53(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 Au Cl 177.1(4) . . ?
N1 C1 N2 105.8(11) . . ?
N1 C1 Au 121.7(10) . . ?
N2 C1 Au 132.0(10) . . ?
C16 C21 C22 111.7(15) . . ?
C16 C21 C23 109.0(16) . . ?
C22 C21 C23 112.2(19) . . ?
C3 C2 N1 107.0(12) . . ?
O1 C8 C7 108.0(11) . . ?
O1 C8 C9 108.3(11) . . ?
C7 C8 C9 113.9(11) . . ?
C16 C15 C20 122.8(14) . . ?
C16 C15 N1 118.5(13) . . ?
C20 C15 N1 118.6(13) . . ?
C5 C4 C3 118.7(14) . . ?
C7 N2 C1 130.3(12) . . ?
C7 N2 C3 121.3(12) . . ?
C1 N2 C3 108.4(11) . . ?
C7 C6 C5 121.8(13) . . ?
C8 C9 C10 109.8(12) . . ?
C8 C9 C12 108.3(13) . . ?
C10 C9 C12 108.3(13) . . ?
C8 C9 C11 112.9(13) . . ?
C10 C9 C11 109.2(13) . . ?
C12 C9 C11 108.2(13) . . ?
C6 C7 N2 118.1(13) . . ?
C6 C7 C8 121.4(12) . . ?
N2 C7 C8 120.3(12) . . ?
C4 C5 C6 120.6(13) . . ?
C1 N1 C2 111.2(11) . . ?
C1 N1 C15 124.0(11) . . ?
C2 N1 C15 124.8(12) . . ?
C2 C3 N2 107.5(12) . . ?
C2 C3 C4 133.7(14) . . ?
N2 C3 C4 118.7(13) . . ?
C17 C16 C15 117.6(15) . . ?
C17 C16 C21 120.1(14) . . ?
C15 C16 C21 122.2(14) . . ?
C18 C17 C16 121.3(16) . . ?
C19 C20 C15 117.4(15) . . ?
C19 C20 C24 121.1(15) . . ?
C15 C20 C24 121.5(14) . . ?
C13 O1 C8 117.5(11) . . ?
O2 C13 O1 122.8(13) . . ?
O2 C13 C14 126.3(14) . . ?
O1 C13 C14 110.9(12) . . ?
C18 C19 C20 120.9(16) . . ?
C17 C18 C19 120.0(15) . . ?
C20 C24 C26 111.6(13) . . ?
C20 C24 C25 111.5(15) . . ?
C26 C24 C25 110.9(15) . . ?

_refine_diff_density_max         2.630
_refine_diff_density_min         -2.891
_refine_diff_density_rms         0.200



####################################################################### 
# 
# 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_shelx_CCDC5
_database_code_depnum_ccdc_archive 'CCDC 2167550'
loop_
_audit_author_name
_audit_author_address
'Magda Monari'
;University of Bologna
Italy
;
_audit_update_record             
;
2022-04-19 deposited with the CCDC.	2022-06-28 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         ?
_chemical_formula_sum            'C25 H34 Au Cl N2 O'
_chemical_formula_weight         610.96

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

_cell_length_a                   10.1180(14)
_cell_length_b                   12.9400(18)
_cell_length_c                   19.485(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2551.1(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9933
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      28.35

_exptl_crystal_description       prism
_exptl_crystal_colour            pale-yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.591
_exptl_crystal_F_000             1208
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.14
_exptl_absorpt_coefficient_mu    5.889
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6587
_exptl_absorpt_correction_T_max  0.7639
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33295
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.889
_diffrn_reflns_theta_max         25.993
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4997
_reflns_number_gt                4963
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.766
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0272P)²+7.1063P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.479(9)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4997
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0202
_refine_ls_R_factor_gt           0.0200
_refine_ls_wR_factor_ref         0.0537
_refine_ls_wR_factor_gt          0.0535
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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
Au Au 0.20411(2) 0.31556(2) 0.28839(2) 0.01459(7) Uani 1 1 d . . . . .
Cl Cl 0.33993(15) 0.43313(12) 0.33913(8) 0.0230(3) Uani 1 1 d . . . . .
C13 C 0.2171(8) 0.4239(5) 0.0653(4) 0.0308(15) Uani 1 1 d . . . . .
H13A H 0.125571 0.399529 0.062437 0.046 Uiso 1 1 calc R U . . .
H13B H 0.237703 0.465854 0.024817 0.046 Uiso 1 1 calc R U . . .
H13C H 0.228289 0.465720 0.106803 0.046 Uiso 1 1 calc R U . . .
N1 N -0.0043(5) 0.1562(3) 0.2744(2) 0.0130(10) Uani 1 1 d . . . . .
N2 N 0.0809(4) 0.1823(4) 0.1743(2) 0.0163(9) Uani 1 1 d . . . . .
C19 C 0.0693(6) 0.1011(5) 0.3879(3) 0.0182(13) Uani 1 1 d . . . . .
C12 C 0.3952(6) 0.1332(5) 0.1968(3) 0.0206(13) Uani 1 1 d . . . . .
H12A H 0.471941 0.087152 0.199154 0.031 Uiso 1 1 calc R U . . .
H12B H 0.314780 0.092080 0.190506 0.031 Uiso 1 1 calc R U . . .
H12C H 0.388500 0.172809 0.239556 0.031 Uiso 1 1 calc R U . . .
C1 C 0.0899(5) 0.2120(4) 0.2418(3) 0.0135(11) Uani 1 1 d . . . . .
O1 O 0.3037(4) 0.3377(3) 0.0679(2) 0.0208(8) Uani 1 1 d . . . . .
C7 C 0.1596(6) 0.2103(5) 0.1175(3) 0.0161(12) Uani 1 1 d . . . . .
C3 C -0.0224(6) 0.1101(5) 0.1666(3) 0.0174(12) Uani 1 1 d . . . . .
C5 C 0.0162(6) 0.1045(5) 0.0457(3) 0.0231(14) Uani 1 1 d . . . . .
H5 H -0.006138 0.081820 0.000847 0.028 Uiso 1 1 calc R U . . .
C6 C 0.1236(6) 0.1723(5) 0.0554(3) 0.0216(12) Uani 1 1 d . . . . .
H6 H 0.173536 0.192365 0.016313 0.026 Uiso 1 1 calc R U . . .
C18 C 0.0516(7) 0.1030(5) 0.4582(3) 0.0251(14) Uani 1 1 d . . . . .
H18 H 0.112335 0.067132 0.486804 0.030 Uiso 1 1 calc R U . . .
C14 C -0.0228(6) 0.1564(4) 0.3483(3) 0.0158(12) Uani 1 1 d . . . . .
C8 C 0.2841(6) 0.2741(4) 0.1269(3) 0.0182(11) Uani 1 1 d . . . . .
H8 H 0.273219 0.319398 0.168051 0.022 Uiso 1 1 calc R U . . .
C17 C -0.0520(7) 0.1557(5) 0.4878(3) 0.0261(15) Uani 1 1 d . . . . .
H17 H -0.061778 0.155970 0.536314 0.031 Uiso 1 1 calc R U . . .
C4 C -0.0555(6) 0.0715(5) 0.1004(3) 0.0232(13) Uani 1 1 d . . . . .
H4 H -0.126057 0.023871 0.094661 0.028 Uiso 1 1 calc R U . . .
C2 C -0.0740(6) 0.0936(5) 0.2301(3) 0.0182(12) Uani 1 1 d . . . . .
H2 H -0.144085 0.047901 0.241635 0.022 Uiso 1 1 calc R U . . .
C10 C 0.5258(6) 0.2816(5) 0.1506(4) 0.0265(14) Uani 1 1 d . . . . .
H10A H 0.606692 0.241555 0.158326 0.040 Uiso 1 1 calc R U . . .
H10B H 0.505730 0.322440 0.191668 0.040 Uiso 1 1 calc R U . . .
H10C H 0.538604 0.327988 0.111414 0.040 Uiso 1 1 calc R U . . .
C11 C 0.4416(7) 0.1456(5) 0.0713(4) 0.0258(14) Uani 1 1 d . . . . .
H11A H 0.445847 0.191962 0.031635 0.039 Uiso 1 1 calc R U . . .
H11B H 0.371626 0.094348 0.064160 0.039 Uiso 1 1 calc R U . . .
H11C H 0.526567 0.110249 0.076845 0.039 Uiso 1 1 calc R U . . .
C9 C 0.4115(6) 0.2082(4) 0.1358(3) 0.0176(12) Uani 1 1 d . . . . .
C23 C 0.1793(6) 0.0380(5) 0.3556(3) 0.0233(13) Uani 1 1 d . . . . .
H23 H 0.185537 0.058592 0.306256 0.028 Uiso 1 1 calc R U . . .
C15 C -0.1287(6) 0.2087(4) 0.3757(3) 0.0182(12) Uani 1 1 d . . . . .
C16 C -0.1411(7) 0.2079(5) 0.4476(3) 0.0240(14) Uani 1 1 d . . . . .
H16 H -0.212226 0.243952 0.468552 0.029 Uiso 1 1 calc R U . . .
C20 C -0.2315(6) 0.2646(5) 0.3330(4) 0.0253(14) Uani 1 1 d . . . . .
H20 H -0.206352 0.256417 0.283647 0.030 Uiso 1 1 calc R U . . .
C22 C -0.3678(8) 0.2163(8) 0.3425(5) 0.046(2) Uani 1 1 d . . . . .
H22A H -0.367572 0.145970 0.323874 0.069 Uiso 1 1 calc R U . . .
H22B H -0.433826 0.257939 0.318153 0.069 Uiso 1 1 calc R U . . .
H22C H -0.389593 0.214132 0.391445 0.069 Uiso 1 1 calc R U . . .
C24 C 0.1465(7) -0.0777(6) 0.3580(4) 0.0356(17) Uani 1 1 d . . . . .
H24A H 0.146203 -0.101356 0.405754 0.053 Uiso 1 1 calc R U . . .
H24B H 0.213107 -0.116353 0.332001 0.053 Uiso 1 1 calc R U . . .
H24C H 0.059128 -0.089391 0.337651 0.053 Uiso 1 1 calc R U . . .
C21 C -0.2359(12) 0.3792(7) 0.3485(6) 0.064(3) Uani 1 1 d . . . . .
H21A H -0.260437 0.389590 0.396706 0.097 Uiso 1 1 calc R U . . .
H21B H -0.301455 0.412562 0.318865 0.097 Uiso 1 1 calc R U . . .
H21C H -0.148718 0.409643 0.340113 0.097 Uiso 1 1 calc R U . . .
C25 C 0.3137(7) 0.0600(7) 0.3890(5) 0.0427(19) Uani 1 1 d . . . . .
H25A H 0.329461 0.134745 0.389744 0.064 Uiso 1 1 calc R U . . .
H25B H 0.383656 0.026057 0.362473 0.064 Uiso 1 1 calc R U . . .
H25C H 0.313992 0.033322 0.436051 0.064 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
Au C1 1.989(6) . ?
Au Cl 2.2760(15) . ?
C13 O1 1.419(8) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
N1 C1 1.354(7) . ?
N1 C2 1.378(7) . ?
N1 C14 1.453(7) . ?
N2 C1 1.373(7) . ?
N2 C7 1.411(7) . ?
N2 C3 1.410(8) . ?
C19 C18 1.382(9) . ?
C19 C14 1.405(8) . ?
C19 C23 1.517(9) . ?
C12 C9 1.545(8) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
O1 C8 1.427(7) . ?
C7 C6 1.356(9) . ?
C7 C8 1.518(8) . ?
C3 C2 1.360(9) . ?
C3 C4 1.422(8) . ?
C5 C4 1.358(9) . ?
C5 C6 1.409(9) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C18 C17 1.377(10) . ?
C18 H18 0.9500 . ?
C14 C15 1.375(9) . ?
C8 C9 1.555(8) . ?
C8 H8 1.0000 . ?
C17 C16 1.373(10) . ?
C17 H17 0.9500 . ?
C4 H4 0.9500 . ?
C2 H2 0.9500 . ?
C10 C9 1.524(8) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C9 1.525(9) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C23 C24 1.535(10) . ?
C23 C25 1.534(9) . ?
C23 H23 1.0000 . ?
C15 C16 1.406(8) . ?
C15 C20 1.515(9) . ?
C16 H16 0.9500 . ?
C20 C22 1.525(10) . ?
C20 C21 1.515(10) . ?
C20 H20 1.0000 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Au Cl 178.15(17) . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C1 N1 C2 112.3(5) . . ?
C1 N1 C14 123.7(5) . . ?
C2 N1 C14 123.8(5) . . ?
C1 N2 C7 130.0(5) . . ?
C1 N2 C3 109.7(5) . . ?
C7 N2 C3 120.3(5) . . ?
C18 C19 C14 116.7(6) . . ?
C18 C19 C23 121.1(6) . . ?
C14 C19 C23 122.2(6) . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C1 N2 104.7(5) . . ?
N1 C1 Au 123.7(4) . . ?
N2 C1 Au 131.6(4) . . ?
C13 O1 C8 113.4(5) . . ?
C6 C7 N2 117.1(5) . . ?
C6 C7 C8 121.8(5) . . ?
N2 C7 C8 120.9(5) . . ?
C2 C3 C4 132.8(6) . . ?
C2 C3 N2 107.0(5) . . ?
C4 C3 N2 120.2(5) . . ?
C4 C5 C6 120.2(6) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C7 C6 C5 123.5(6) . . ?
C7 C6 H6 118.3 . . ?
C5 C6 H6 118.3 . . ?
C19 C18 C17 121.5(6) . . ?
C19 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?
C15 C14 C19 123.7(5) . . ?
C15 C14 N1 119.0(5) . . ?
C19 C14 N1 117.2(5) . . ?
O1 C8 C7 109.4(5) . . ?
O1 C8 C9 106.9(5) . . ?
C7 C8 C9 113.8(4) . . ?
O1 C8 H8 108.9 . . ?
C7 C8 H8 108.9 . . ?
C9 C8 H8 108.9 . . ?
C16 C17 C18 120.3(6) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C5 C4 C3 118.4(6) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
C3 C2 N1 106.3(5) . . ?
C3 C2 H2 126.8 . . ?
N1 C2 H2 126.8 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C9 C11 109.6(5) . . ?
C10 C9 C12 109.0(5) . . ?
C11 C9 C12 108.7(5) . . ?
C10 C9 C8 108.0(5) . . ?
C11 C9 C8 111.4(5) . . ?
C12 C9 C8 110.0(5) . . ?
C19 C23 C24 110.7(5) . . ?
C19 C23 C25 112.0(6) . . ?
C24 C23 C25 111.1(6) . . ?
C19 C23 H23 107.6 . . ?
C24 C23 H23 107.6 . . ?
C25 C23 H23 107.6 . . ?
C14 C15 C16 116.9(6) . . ?
C14 C15 C20 123.9(5) . . ?
C16 C15 C20 119.3(6) . . ?
C17 C16 C15 120.9(6) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C15 C20 C22 111.0(6) . . ?
C15 C20 C21 112.2(7) . . ?
C22 C20 C21 110.5(7) . . ?
C15 C20 H20 107.6 . . ?
C22 C20 H20 107.6 . . ?
C21 C20 H20 107.6 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 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
C2 N1 C1 N2 -1.0(6) . . . . ?
C14 N1 C1 N2 174.5(5) . . . . ?
C2 N1 C1 Au 177.0(4) . . . . ?
C14 N1 C1 Au -7.5(7) . . . . ?
C7 N2 C1 N1 -175.8(6) . . . . ?
C3 N2 C1 N1 1.7(6) . . . . ?
C7 N2 C1 Au 6.4(10) . . . . ?
C3 N2 C1 Au -176.1(4) . . . . ?
C1 N2 C7 C6 -177.0(6) . . . . ?
C3 N2 C7 C6 5.7(8) . . . . ?
C1 N2 C7 C8 7.2(9) . . . . ?
C3 N2 C7 C8 -170.1(5) . . . . ?
C1 N2 C3 C2 -1.8(7) . . . . ?
C7 N2 C3 C2 176.0(5) . . . . ?
C1 N2 C3 C4 176.9(6) . . . . ?
C7 N2 C3 C4 -5.3(9) . . . . ?
N2 C7 C6 C5 -2.2(9) . . . . ?
C8 C7 C6 C5 173.6(6) . . . . ?
C4 C5 C6 C7 -1.8(10) . . . . ?
C14 C19 C18 C17 0.6(9) . . . . ?
C23 C19 C18 C17 -176.6(6) . . . . ?
C18 C19 C14 C15 -1.6(9) . . . . ?
C23 C19 C14 C15 175.6(6) . . . . ?
C18 C19 C14 N1 179.2(5) . . . . ?
C23 C19 C14 N1 -3.7(8) . . . . ?
C1 N1 C14 C15 105.8(6) . . . . ?
C2 N1 C14 C15 -79.2(7) . . . . ?
C1 N1 C14 C19 -74.9(7) . . . . ?
C2 N1 C14 C19 100.1(7) . . . . ?
C13 O1 C8 C7 75.2(6) . . . . ?
C13 O1 C8 C9 -161.2(5) . . . . ?
C6 C7 C8 O1 36.2(8) . . . . ?
N2 C7 C8 O1 -148.2(5) . . . . ?
C6 C7 C8 C9 -83.4(7) . . . . ?
N2 C7 C8 C9 92.3(7) . . . . ?
C19 C18 C17 C16 0.2(10) . . . . ?
C6 C5 C4 C3 2.3(10) . . . . ?
C2 C3 C4 C5 179.5(7) . . . . ?
N2 C3 C4 C5 1.1(9) . . . . ?
C4 C3 C2 N1 -177.4(7) . . . . ?
N2 C3 C2 N1 1.1(7) . . . . ?
C1 N1 C2 C3 -0.1(7) . . . . ?
C14 N1 C2 C3 -175.6(5) . . . . ?
O1 C8 C9 C10 63.8(6) . . . . ?
C7 C8 C9 C10 -175.3(5) . . . . ?
O1 C8 C9 C11 -56.6(6) . . . . ?
C7 C8 C9 C11 64.3(7) . . . . ?
O1 C8 C9 C12 -177.3(5) . . . . ?
C7 C8 C9 C12 -56.4(6) . . . . ?
C18 C19 C23 C24 73.8(8) . . . . ?
C14 C19 C23 C24 -103.2(7) . . . . ?
C18 C19 C23 C25 -50.8(8) . . . . ?
C14 C19 C23 C25 132.2(6) . . . . ?
C19 C14 C15 C16 1.7(9) . . . . ?
N1 C14 C15 C16 -179.1(5) . . . . ?
C19 C14 C15 C20 -177.3(6) . . . . ?
N1 C14 C15 C20 1.9(8) . . . . ?
C18 C17 C16 C15 0.0(10) . . . . ?
C14 C15 C16 C17 -0.9(9) . . . . ?
C20 C15 C16 C17 178.2(6) . . . . ?
C14 C15 C20 C22 116.8(7) . . . . ?
C16 C15 C20 C22 -62.2(8) . . . . ?
C14 C15 C20 C21 -119.0(8) . . . . ?
C16 C15 C20 C21 62.0(9) . . . . ?

_refine_diff_density_max         2.423
_refine_diff_density_min         -1.083
_refine_diff_density_rms         0.097



####################################################################### 
# 
# 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_shelx_CCDC6
_database_code_depnum_ccdc_archive 'CCDC 2167553'
loop_
_audit_author_name
_audit_author_address
'Magda Monari'
;University of Bologna
Italy
;
_audit_update_record             
;
2022-04-19 deposited with the CCDC.	2022-06-28 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         ?
_chemical_formula_sum            'C13 H11 N O2'
_chemical_formula_weight         213.23

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   18.8360(12)
_cell_length_b                   7.3826(5)
_cell_length_c                   17.1906(11)
_cell_angle_alpha                90
_cell_angle_beta                 115.5420(10)
_cell_angle_gamma                90
_cell_volume                     2156.9(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7851
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      30.63

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_F_000             896
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7326
_exptl_absorpt_correction_T_max  0.9114
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12671
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.397
_diffrn_reflns_theta_max         25.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             1957
_reflns_number_gt                1747
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0506P)²+4.0562P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1957
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0641
_refine_ls_wR_factor_ref         0.1603
_refine_ls_wR_factor_gt          0.1569
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_restrained_S_all      1.116
_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
O1 O 0.71576(10) 0.4260(3) 0.71833(11) 0.0526(5) Uani 1 1 d . . . . .
O2 O 0.78132(11) 0.4129(3) 0.63932(13) 0.0634(6) Uani 1 1 d . . . . .
N1 N 0.58049(11) 0.3060(3) 0.58186(13) 0.0397(5) Uani 1 1 d . . . . .
C6 C 0.55899(15) 0.2083(4) 0.45019(16) 0.0438(6) Uani 1 1 d . . . . .
C8 C 0.65088(14) 0.3074(3) 0.57545(15) 0.0408(6) Uani 1 1 d . . . . .
C1 C 0.52315(14) 0.2484(3) 0.50487(16) 0.0414(6) Uani 1 1 d . . . . .
C10 C 0.57401(15) 0.3695(4) 0.65802(16) 0.0458(6) Uani 1 1 d . . . . .
H10A H 0.533812 0.301304 0.666350 0.055 Uiso 1 1 calc R U . . .
H10B H 0.559210 0.496426 0.651517 0.055 Uiso 1 1 calc R U . . .
C7 C 0.63986(15) 0.2470(4) 0.49649(16) 0.0468(7) Uani 1 1 d . . . . .
H7 H 0.678356 0.233529 0.476659 0.056 Uiso 1 1 calc R U . . .
C9 C 0.72112(15) 0.3822(4) 0.64488(17) 0.0461(6) Uani 1 1 d . . . . .
C11 C 0.65254(15) 0.3449(4) 0.73479(16) 0.0457(6) Uani 1 1 d . . . . .
H11 H 0.662949 0.215205 0.746032 0.055 Uiso 1 1 calc R U . . .
C2 C 0.44244(15) 0.2265(4) 0.47857(19) 0.0540(7) Uani 1 1 d . . . . .
H2 H 0.419074 0.252642 0.515147 0.065 Uiso 1 1 calc R U . . .
C5 C 0.51224(18) 0.1440(4) 0.36655(18) 0.0569(8) Uani 1 1 d . . . . .
H5 H 0.534690 0.115455 0.329368 0.068 Uiso 1 1 calc R U . . .
C3 C 0.39931(17) 0.1648(4) 0.3963(2) 0.0632(9) Uani 1 1 d . . . . .
H3 H 0.345343 0.149241 0.376779 0.076 Uiso 1 1 calc R U . . .
C12 C 0.65625(18) 0.4348(4) 0.81422(19) 0.0600(8) Uani 1 1 d . . . . .
H12 H 0.646787 0.558704 0.812164 0.072 Uiso 1 1 calc R U . . .
C4 C 0.43359(19) 0.1245(4) 0.34107(19) 0.0631(9) Uani 1 1 d . . . . .
H4 H 0.402070 0.083330 0.285638 0.076 Uiso 1 1 calc R U . . .
C13 C 0.6718(2) 0.3510(6) 0.8854(2) 0.0846(12) Uani 1 1 d . . . . .
H13A H 0.681482 0.227079 0.889460 0.101 Uiso 1 1 calc R U . . .
H13B H 0.673242 0.414521 0.932832 0.101 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
O1 C9 1.349(3) . ?
O1 C11 1.465(3) . ?
O2 C9 1.200(3) . ?
N1 C1 1.366(3) . ?
N1 C8 1.377(3) . ?
N1 C10 1.445(3) . ?
C6 C5 1.406(4) . ?
C6 C1 1.405(4) . ?
C6 C7 1.411(4) . ?
C8 C7 1.357(4) . ?
C8 C9 1.455(4) . ?
C1 C2 1.396(4) . ?
C10 C11 1.510(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C7 H7 0.9300 . ?
C11 C12 1.492(4) . ?
C11 H11 0.9800 . ?
C2 C3 1.370(4) . ?
C2 H2 0.9300 . ?
C5 C4 1.360(4) . ?
C5 H5 0.9300 . ?
C3 C4 1.392(5) . ?
C3 H3 0.9300 . ?
C12 C13 1.287(4) . ?
C12 H12 0.9300 . ?
C4 H4 0.9300 . ?
C13 H13A 0.9300 . ?
C13 H13B 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 O1 C11 118.5(2) . . ?
C1 N1 C8 108.1(2) . . ?
C1 N1 C10 129.7(2) . . ?
C8 N1 C10 122.0(2) . . ?
C5 C6 C1 119.1(2) . . ?
C5 C6 C7 133.9(3) . . ?
C1 C6 C7 107.1(2) . . ?
C7 C8 N1 109.9(2) . . ?
C7 C8 C9 129.6(2) . . ?
N1 C8 C9 120.2(2) . . ?
N1 C1 C2 130.2(3) . . ?
N1 C1 C6 107.8(2) . . ?
C2 C1 C6 122.0(2) . . ?
N1 C10 C11 108.6(2) . . ?
N1 C10 H10A 110.0 . . ?
C11 C10 H10A 110.0 . . ?
N1 C10 H10B 110.0 . . ?
C11 C10 H10B 110.0 . . ?
H10A C10 H10B 108.3 . . ?
C8 C7 C6 107.0(2) . . ?
C8 C7 H7 126.5 . . ?
C6 C7 H7 126.5 . . ?
O2 C9 O1 119.0(2) . . ?
O2 C9 C8 124.2(3) . . ?
O1 C9 C8 116.8(2) . . ?
O1 C11 C12 105.9(2) . . ?
O1 C11 C10 110.7(2) . . ?
C12 C11 C10 112.8(2) . . ?
O1 C11 H11 109.1 . . ?
C12 C11 H11 109.1 . . ?
C10 C11 H11 109.1 . . ?
C3 C2 C1 116.8(3) . . ?
C3 C2 H2 121.6 . . ?
C1 C2 H2 121.6 . . ?
C4 C5 C6 118.7(3) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C2 C3 C4 122.2(3) . . ?
C2 C3 H3 118.9 . . ?
C4 C3 H3 118.9 . . ?
C13 C12 C11 124.0(3) . . ?
C13 C12 H12 118.0 . . ?
C11 C12 H12 118.0 . . ?
C5 C4 C3 121.3(3) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C12 C13 H13A 120.0 . . ?
C12 C13 H13B 120.0 . . ?
H13A C13 H13B 120.0 . . ?

_refine_diff_density_max         0.200
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.038



####################################################################### 
# 
# 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_shelx_CCDC7
_database_code_depnum_ccdc_archive 'CCDC 2167552'
loop_
_audit_author_name
_audit_author_address
'Magda Monari'
;University of Bologna
Italy
;
_audit_update_record             
;
2022-04-19 deposited with the CCDC.	2022-06-28 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         ?
_chemical_formula_sum            'C31 H40 Au Cl N2 O'
_chemical_formula_weight         689.06

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      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                   12.7402(8)
_cell_length_b                   13.7979(8)
_cell_length_c                   16.0681(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2824.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9352
_cell_measurement_theta_min      2.93
_cell_measurement_theta_max      30.53

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.620
_exptl_crystal_F_000             1376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    5.329
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3475
_exptl_absorpt_correction_T_max  0.7411
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            63032
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_av_R_equivalents  0.0600
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.945
_diffrn_reflns_theta_max         30.572
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8646
_reflns_number_gt                8471
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.803
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.999

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0059P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_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 3673 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.052(3)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         8646
_refine_ls_number_parameters     330
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0176
_refine_ls_R_factor_gt           0.0169
_refine_ls_wR_factor_ref         0.0385
_refine_ls_wR_factor_gt          0.0384
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.004
_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 0.83919(2) 0.60582(2) 0.40885(2) 0.01120(3) Uani 1 1 d . . . . .
Cl1 Cl 0.97362(6) 0.55087(6) 0.32788(5) 0.01997(15) Uani 1 1 d . . . . .
O1 O 0.89190(17) 0.44122(16) 0.62619(14) 0.0159(4) Uani 1 1 d . . . . .
N1 N 0.6708(2) 0.73644(17) 0.47135(15) 0.0124(5) Uani 1 1 d . . . . .
N2 N 0.72013(19) 0.64314(18) 0.57105(15) 0.0113(5) Uani 1 1 d . . . . .
C1 C 0.7323(2) 0.6586(2) 0.48713(17) 0.0107(5) Uani 1 1 d . . . . .
C9 C 0.7234(2) 0.3939(2) 0.56966(16) 0.0119(5) Uani 1 1 d . . . . .
C7 C 0.7599(2) 0.5670(2) 0.62110(19) 0.0132(5) Uani 1 1 d . . . . .
C19 C 0.6511(2) 0.7724(2) 0.38811(17) 0.0130(5) Uani 1 1 d . . . . .
C3 C 0.6558(2) 0.7160(2) 0.60622(17) 0.0126(5) Uani 1 1 d . . . . .
C2 C 0.6243(2) 0.7734(2) 0.54163(19) 0.0142(6) Uani 1 1 d . . . . .
H2 H 0.579168 0.828045 0.544720 0.017 Uiso 1 1 calc R U . . .
C4 C 0.6407(2) 0.7200(2) 0.6935(2) 0.0173(6) Uani 1 1 d . . . . .
H4 H 0.599456 0.769909 0.717796 0.021 Uiso 1 1 calc R U . . .
C10 C 0.7713(2) 0.3187(2) 0.5097(2) 0.0171(6) Uani 1 1 d . . . . .
H10A H 0.790204 0.350708 0.456652 0.021 Uiso 1 1 calc R U . . .
H10B H 0.836155 0.291609 0.534421 0.021 Uiso 1 1 calc R U . . .
C13 C 0.5441(3) 0.3513(2) 0.5145(2) 0.0187(6) Uani 1 1 d . . . . .
H13 H 0.478549 0.378495 0.489442 0.022 Uiso 1 1 calc R U . . .
C31 C 0.9849(3) 0.4936(2) 0.6080(2) 0.0208(7) Uani 1 1 d . . . . .
H31A H 0.998573 0.491050 0.547986 0.031 Uiso 1 1 calc R U . . .
H31B H 1.044040 0.464778 0.638047 0.031 Uiso 1 1 calc R U . . .
H31C H 0.976242 0.561273 0.625250 0.031 Uiso 1 1 calc R U . . .
C22 C 0.6103(3) 0.8398(2) 0.2312(2) 0.0218(7) Uani 1 1 d . . . . .
H22 H 0.596107 0.862958 0.176681 0.026 Uiso 1 1 calc R U . . .
C6 C 0.7442(3) 0.5743(2) 0.70451(19) 0.0172(6) Uani 1 1 d . . . . .
H6 H 0.773176 0.525863 0.739631 0.021 Uiso 1 1 calc R U . . .
C5 C 0.6862(3) 0.6512(2) 0.74179(19) 0.0192(7) Uani 1 1 d . . . . .
H5 H 0.679454 0.654316 0.800613 0.023 Uiso 1 1 calc R U . . .
C16 C 0.6664(3) 0.1866(2) 0.5750(2) 0.0240(7) Uani 1 1 d . . . . .
H16A H 0.730817 0.158591 0.599689 0.029 Uiso 1 1 calc R U . . .
H16B H 0.616012 0.133350 0.564856 0.029 Uiso 1 1 calc R U . . .
C28 C 0.8039(2) 0.8893(2) 0.4060(2) 0.0192(5) Uani 1 1 d . . . . .
H28 H 0.812334 0.849783 0.457696 0.023 Uiso 1 1 calc R U . . .
C14 C 0.6219(3) 0.4334(2) 0.5306(2) 0.0158(6) Uani 1 1 d . . . . .
H14A H 0.589821 0.481544 0.568569 0.019 Uiso 1 1 calc R U . . .
H14B H 0.638568 0.466360 0.477549 0.019 Uiso 1 1 calc R U . . .
C8 C 0.8047(2) 0.4768(2) 0.58017(18) 0.0126(5) Uani 1 1 d . . . . .
H8 H 0.830329 0.495363 0.523526 0.015 Uiso 1 1 calc R U . . .
C24 C 0.7144(2) 0.8468(2) 0.3569(2) 0.0151(6) Uani 1 1 d . . . . .
C11 C 0.6932(3) 0.2368(2) 0.4928(2) 0.0204(7) Uani 1 1 d . . . . .
H11 H 0.725335 0.188789 0.453758 0.024 Uiso 1 1 calc R U . . .
C29 C 0.9068(3) 0.8845(3) 0.3581(2) 0.0303(8) Uani 1 1 d . . . . .
H29A H 0.921539 0.817054 0.342813 0.045 Uiso 1 1 calc R U . . .
H29B H 0.963834 0.909223 0.393119 0.045 Uiso 1 1 calc R U . . .
H29C H 0.901423 0.923952 0.307616 0.045 Uiso 1 1 calc R U . . .
C12 C 0.5932(3) 0.2782(2) 0.4542(2) 0.0214(7) Uani 1 1 d . . . . .
H12A H 0.542896 0.225171 0.442713 0.026 Uiso 1 1 calc R U . . .
H12B H 0.610154 0.310549 0.400846 0.026 Uiso 1 1 calc R U . . .
C20 C 0.5679(2) 0.7305(2) 0.34360(19) 0.0152(6) Uani 1 1 d . . . . .
C21 C 0.5493(3) 0.7663(2) 0.2641(2) 0.0195(6) Uani 1 1 d . . . . .
H21 H 0.493762 0.739822 0.231818 0.023 Uiso 1 1 calc R U . . .
C23 C 0.6914(2) 0.8799(2) 0.2764(2) 0.0196(6) Uani 1 1 d . . . . .
H23 H 0.732227 0.930589 0.252779 0.024 Uiso 1 1 calc R U . . .
C25 C 0.5047(2) 0.6466(2) 0.3770(2) 0.0185(6) Uani 1 1 d . . . . .
H25 H 0.517247 0.642991 0.438393 0.022 Uiso 1 1 calc R U . . .
C18 C 0.6185(3) 0.2603(2) 0.6349(2) 0.0217(7) Uani 1 1 d . . . . .
H18 H 0.601245 0.227303 0.688591 0.026 Uiso 1 1 calc R U . . .
C17 C 0.5175(3) 0.3012(2) 0.5967(2) 0.0228(6) Uani 1 1 d . . . . .
H17A H 0.466772 0.248072 0.586755 0.027 Uiso 1 1 calc R U . . .
H17B H 0.484952 0.348198 0.635493 0.027 Uiso 1 1 calc R U . . .
C30 C 0.7793(3) 0.9935(3) 0.4323(3) 0.0417(12) Uani 1 1 d . . . . .
H30A H 0.764454 1.032648 0.382794 0.063 Uiso 1 1 calc R U . . .
H30B H 0.839658 1.020723 0.461909 0.063 Uiso 1 1 calc R U . . .
H30C H 0.717839 0.993665 0.469008 0.063 Uiso 1 1 calc R U . . .
C15 C 0.6959(3) 0.3431(2) 0.65184(19) 0.0165(6) Uani 1 1 d . . . . .
H15A H 0.664126 0.390184 0.690880 0.020 Uiso 1 1 calc R U . . .
H15B H 0.760506 0.316954 0.677722 0.020 Uiso 1 1 calc R U . . .
C27 C 0.3870(3) 0.6583(3) 0.3634(3) 0.0346(9) Uani 1 1 d . . . . .
H27A H 0.362864 0.717727 0.390691 0.052 Uiso 1 1 calc R U . . .
H27B H 0.350119 0.602415 0.387161 0.052 Uiso 1 1 calc R U . . .
H27C H 0.372434 0.662110 0.303622 0.052 Uiso 1 1 calc R U . . .
C26 C 0.5442(3) 0.5523(3) 0.3386(2) 0.0251(7) Uani 1 1 d . . . . .
H26A H 0.534384 0.554390 0.278141 0.038 Uiso 1 1 calc R U . . .
H26B H 0.504722 0.497608 0.361741 0.038 Uiso 1 1 calc R U . . .
H26C H 0.618983 0.544214 0.351242 0.038 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 1.992(3) . ?
Au1 Cl1 2.2805(8) . ?
O1 C31 1.418(4) . ?
O1 C8 1.422(3) . ?
N1 C1 1.354(4) . ?
N1 C2 1.373(4) . ?
N1 C19 1.449(3) . ?
N2 C1 1.374(4) . ?
N2 C3 1.414(4) . ?
N2 C7 1.416(4) . ?
C9 C15 1.535(4) . ?
C9 C14 1.536(4) . ?
C9 C10 1.542(4) . ?
C9 C8 1.553(4) . ?
C7 C6 1.359(4) . ?
C7 C8 1.519(4) . ?
C19 C24 1.398(4) . ?
C19 C20 1.403(4) . ?
C3 C2 1.366(4) . ?
C3 C4 1.417(4) . ?
C2 H2 0.9500 . ?
C4 C5 1.355(5) . ?
C4 H4 0.9500 . ?
C10 C11 1.531(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C13 C14 1.527(5) . ?
C13 C17 1.529(5) . ?
C13 C12 1.534(5) . ?
C13 H13 1.0000 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C22 C21 1.382(5) . ?
C22 C23 1.380(5) . ?
C22 H22 0.9500 . ?
C6 C5 1.425(4) . ?
C6 H6 0.9500 . ?
C5 H5 0.9500 . ?
C16 C11 1.529(5) . ?
C16 C18 1.528(5) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C28 C24 1.506(4) . ?
C28 C29 1.521(5) . ?
C28 C30 1.531(5) . ?
C28 H28 1.0000 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C8 H8 1.0000 . ?
C24 C23 1.402(4) . ?
C11 C12 1.527(5) . ?
C11 H11 1.0000 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C20 C21 1.390(4) . ?
C20 C25 1.509(5) . ?
C21 H21 0.9500 . ?
C23 H23 0.9500 . ?
C25 C27 1.524(5) . ?
C25 C26 1.526(5) . ?
C25 H25 1.0000 . ?
C18 C17 1.534(5) . ?
C18 C15 1.533(4) . ?
C18 H18 1.0000 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Au1 Cl1 174.47(8) . . ?
C31 O1 C8 111.6(2) . . ?
C1 N1 C2 113.0(2) . . ?
C1 N1 C19 123.0(2) . . ?
C2 N1 C19 123.9(2) . . ?
C1 N2 C3 110.3(2) . . ?
C1 N2 C7 129.2(3) . . ?
C3 N2 C7 120.5(2) . . ?
N1 C1 N2 104.0(2) . . ?
N1 C1 Au1 124.6(2) . . ?
N2 C1 Au1 129.8(2) . . ?
C15 C9 C14 108.7(2) . . ?
C15 C9 C10 108.7(3) . . ?
C14 C9 C10 108.5(2) . . ?
C15 C9 C8 113.3(2) . . ?
C14 C9 C8 110.2(3) . . ?
C10 C9 C8 107.4(2) . . ?
C6 C7 N2 116.9(3) . . ?
C6 C7 C8 122.9(3) . . ?
N2 C7 C8 119.7(3) . . ?
C24 C19 C20 123.7(3) . . ?
C24 C19 N1 118.9(3) . . ?
C20 C19 N1 117.4(3) . . ?
C2 C3 N2 106.2(2) . . ?
C2 C3 C4 133.6(3) . . ?
N2 C3 C4 120.1(3) . . ?
C3 C2 N1 106.4(3) . . ?
C3 C2 H2 126.8 . . ?
N1 C2 H2 126.8 . . ?
C5 C4 C3 118.7(3) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C11 C10 C9 110.5(3) . . ?
C11 C10 H10A 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
C14 C13 C17 109.5(3) . . ?
C14 C13 C12 109.3(3) . . ?
C17 C13 C12 109.8(3) . . ?
C14 C13 H13 109.4 . . ?
C17 C13 H13 109.4 . . ?
C12 C13 H13 109.4 . . ?
O1 C31 H31A 109.5 . . ?
O1 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
O1 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C21 C22 C23 121.0(3) . . ?
C21 C22 H22 119.5 . . ?
C23 C22 H22 119.5 . . ?
C7 C6 C5 123.1(3) . . ?
C7 C6 H6 118.4 . . ?
C5 C6 H6 118.4 . . ?
C4 C5 C6 120.2(3) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C11 C16 C18 109.4(3) . . ?
C11 C16 H16A 109.8 . . ?
C18 C16 H16A 109.8 . . ?
C11 C16 H16B 109.8 . . ?
C18 C16 H16B 109.8 . . ?
H16A C16 H16B 108.2 . . ?
C24 C28 C29 111.8(3) . . ?
C24 C28 C30 110.8(3) . . ?
C29 C28 C30 111.0(3) . . ?
C24 C28 H28 107.7 . . ?
C29 C28 H28 107.7 . . ?
C30 C28 H28 107.7 . . ?
C13 C14 C9 110.6(3) . . ?
C13 C14 H14A 109.5 . . ?
C9 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C9 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
O1 C8 C7 110.6(2) . . ?
O1 C8 C9 108.9(2) . . ?
C7 C8 C9 113.5(2) . . ?
O1 C8 H8 107.9 . . ?
C7 C8 H8 107.9 . . ?
C9 C8 H8 107.9 . . ?
C19 C24 C23 116.8(3) . . ?
C19 C24 C28 122.3(3) . . ?
C23 C24 C28 120.9(3) . . ?
C12 C11 C16 109.6(3) . . ?
C12 C11 C10 109.7(3) . . ?
C16 C11 C10 109.0(3) . . ?
C12 C11 H11 109.5 . . ?
C16 C11 H11 109.5 . . ?
C10 C11 H11 109.5 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C11 C12 C13 109.2(3) . . ?
C11 C12 H12A 109.8 . . ?
C13 C12 H12A 109.8 . . ?
C11 C12 H12B 109.8 . . ?
C13 C12 H12B 109.8 . . ?
H12A C12 H12B 108.3 . . ?
C21 C20 C19 116.8(3) . . ?
C21 C20 C25 120.5(3) . . ?
C19 C20 C25 122.5(3) . . ?
C22 C21 C20 121.0(3) . . ?
C22 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?
C22 C23 C24 120.7(3) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C20 C25 C27 113.1(3) . . ?
C20 C25 C26 109.5(3) . . ?
C27 C25 C26 110.9(3) . . ?
C20 C25 H25 107.7 . . ?
C27 C25 H25 107.7 . . ?
C26 C25 H25 107.7 . . ?
C16 C18 C17 109.1(3) . . ?
C16 C18 C15 110.5(3) . . ?
C17 C18 C15 109.7(3) . . ?
C16 C18 H18 109.2 . . ?
C17 C18 H18 109.2 . . ?
C15 C18 H18 109.2 . . ?
C13 C17 C18 109.0(3) . . ?
C13 C17 H17A 109.9 . . ?
C18 C17 H17A 109.9 . . ?
C13 C17 H17B 109.9 . . ?
C18 C17 H17B 109.9 . . ?
H17A C17 H17B 108.3 . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C9 C15 C18 109.5(3) . . ?
C9 C15 H15A 109.8 . . ?
C18 C15 H15A 109.8 . . ?
C9 C15 H15B 109.8 . . ?
C18 C15 H15B 109.8 . . ?
H15A C15 H15B 108.2 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

_refine_diff_density_max         1.638
_refine_diff_density_min         -0.748
_refine_diff_density_rms         0.083



