# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2021

####################################################################### 
# 
# 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_4b
_database_code_depnum_ccdc_archive 'CCDC 2085270'
loop_
_audit_author_name
_audit_author_address
'Alessandra Crispini'
;University of Calabria
Italy
;
_audit_update_record             
;
2021-05-22 deposited with the CCDC.	2021-08-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H16 Au Cl N2 O'
_chemical_formula_weight         448.69

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      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                   9.012(3)
_cell_length_b                   10.387(4)
_cell_length_c                   16.294(5)
_cell_angle_alpha                90
_cell_angle_beta                 105.724(13)
_cell_angle_gamma                90
_cell_volume                     1468.2(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7370
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      26.91

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.10
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_max          0.42
_exptl_crystal_density_diffrn    2.030
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    10.192
_shelx_estimated_absorpt_T_min   0.100
_shelx_estimated_absorpt_T_max   0.429
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.125
_exptl_absorpt_correction_T_max  0.532
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'omega scan'
_diffrn_reflns_number            23336
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.352
_diffrn_reflns_theta_max         26.956
_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 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3192
_reflns_number_gt                2857
_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    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0161P)²+0.8414P] 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         3192
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0208
_refine_ls_R_factor_gt           0.0166
_refine_ls_wR_factor_ref         0.0391
_refine_ls_wR_factor_gt          0.0378
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Au Au 0.42689(2) 0.20890(2) 0.87560(2) 0.04947(5) Uani 1 1 d . . . . .
Cl Cl 0.26650(10) 0.05794(9) 0.79431(5) 0.0681(2) Uani 1 1 d . . . . .
O O 0.8952(2) 0.3890(2) 0.83773(13) 0.0576(5) Uani 1 1 d . . . . .
N2 N 0.6263(3) 0.3396(2) 1.03238(15) 0.0513(6) Uani 1 1 d . . . . .
N1 N 0.6524(3) 0.4291(2) 0.91836(14) 0.0493(5) Uani 1 1 d . . . . .
C5 C 0.6402(4) 0.4534(3) 0.82755(17) 0.0532(7) Uani 1 1 d . . . . .
H5A H 0.6718 0.5412 0.8208 0.064 Uiso 1 1 calc R U . . .
H5B H 0.5336 0.4441 0.7946 0.064 Uiso 1 1 calc R U . . .
C8 C 0.7072(3) 0.3724(3) 0.69699(17) 0.0452(6) Uani 1 1 d . . . . .
C13 C 0.5950(4) 0.2952(3) 0.6440(2) 0.0584(8) Uani 1 1 d . . . . .
H13 H 0.5414 0.2357 0.6676 0.070 Uiso 1 1 calc R U . . .
C3 C 0.7350(4) 0.4355(3) 1.0579(2) 0.0599(8) Uani 1 1 d . . . . .
H3 H 0.7862 0.4576 1.1137 0.072 Uiso 1 1 calc R U . . .
C10 C 0.7522(4) 0.4714(3) 0.57215(19) 0.0609(8) Uani 1 1 d . . . . .
H10 H 0.8054 0.5309 0.5482 0.073 Uiso 1 1 calc R U . . .
C9 C 0.7855(3) 0.4610(3) 0.66025(18) 0.0523(7) Uani 1 1 d . . . . .
H9 H 0.8604 0.5135 0.6948 0.063 Uiso 1 1 calc R U . . .
C6 C 0.7403(3) 0.3609(3) 0.79344(17) 0.0471(6) Uani 1 1 d . . . . .
H6 H 0.7168 0.2728 0.8074 0.057 Uiso 1 1 calc R U . . .
C4 C 0.5746(5) 0.2535(4) 1.0907(2) 0.0746(10) Uani 1 1 d . . . . .
H4A H 0.4708 0.2262 1.0645 0.112 Uiso 1 1 calc R U . . .
H4B H 0.5783 0.2985 1.1427 0.112 Uiso 1 1 calc R U . . .
H4C H 0.6409 0.1796 1.1030 0.112 Uiso 1 1 calc R U . . .
C1 C 0.5739(3) 0.3344(3) 0.94609(17) 0.0470(6) Uani 1 1 d . . . . .
C2 C 0.7527(4) 0.4909(3) 0.9861(2) 0.0600(8) Uani 1 1 d . . . . .
H2 H 0.8196 0.5578 0.9829 0.072 Uiso 1 1 calc R U . . .
C12 C 0.5629(4) 0.3069(3) 0.5557(2) 0.0636(8) Uani 1 1 d . . . . .
H12 H 0.4878 0.2550 0.5206 0.076 Uiso 1 1 calc R U . . .
C11 C 0.6417(4) 0.3948(3) 0.52009(19) 0.0607(8) Uani 1 1 d . . . . .
H11 H 0.6203 0.4023 0.4611 0.073 Uiso 1 1 calc R U . . .
C7 C 1.0009(4) 0.2956(4) 0.8225(2) 0.0698(10) Uani 1 1 d . . . . .
H7A H 0.9595 0.2108 0.8247 0.105 Uiso 1 1 calc R U . . .
H7B H 1.0974 0.3032 0.8654 0.105 Uiso 1 1 calc R U . . .
H7C H 1.0167 0.3098 0.7673 0.105 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 1.988(3) . ?
Au Cl 2.2946(10) . ?
O C6 1.417(3) . ?
O C7 1.427(4) . ?
N2 C1 1.358(4) . ?
N2 C3 1.380(4) . ?
N2 C4 1.469(4) . ?
N1 C1 1.358(4) . ?
N1 C2 1.381(4) . ?
N1 C5 1.475(3) . ?
C5 C6 1.522(4) . ?
C8 C9 1.389(4) . ?
C8 C13 1.392(4) . ?
C8 C6 1.523(4) . ?
C13 C12 1.394(5) . ?
C3 C2 1.352(4) . ?
C10 C11 1.374(4) . ?
C10 C9 1.389(4) . ?
C12 C11 1.378(5) . ?

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 177.38(8) . . ?
C6 O C7 112.5(2) . . ?
C1 N2 C3 111.1(2) . . ?
C1 N2 C4 124.3(3) . . ?
C3 N2 C4 124.6(3) . . ?
C1 N1 C2 111.0(2) . . ?
C1 N1 C5 123.6(3) . . ?
C2 N1 C5 125.2(3) . . ?
N1 C5 C6 111.6(2) . . ?
C9 C8 C13 118.8(3) . . ?
C9 C8 C6 121.1(3) . . ?
C13 C8 C6 120.1(3) . . ?
C8 C13 C12 120.2(3) . . ?
C2 C3 N2 106.7(3) . . ?
C11 C10 C9 120.7(3) . . ?
C10 C9 C8 120.3(3) . . ?
O C6 C5 106.5(2) . . ?
O C6 C8 113.5(2) . . ?
C5 C6 C8 111.0(2) . . ?
N2 C1 N1 104.5(3) . . ?
N2 C1 Au 127.9(2) . . ?
N1 C1 Au 127.5(2) . . ?
C3 C2 N1 106.8(3) . . ?
C11 C12 C13 120.3(3) . . ?
C10 C11 C12 119.6(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 C5 C6 -80.7(3) . . . . ?
C2 N1 C5 C6 93.7(3) . . . . ?
C9 C8 C13 C12 0.2(5) . . . . ?
C6 C8 C13 C12 179.0(3) . . . . ?
C1 N2 C3 C2 -0.7(3) . . . . ?
C4 N2 C3 C2 178.9(3) . . . . ?
C11 C10 C9 C8 0.1(5) . . . . ?
C13 C8 C9 C10 -0.3(4) . . . . ?
C6 C8 C9 C10 -179.1(3) . . . . ?
C7 O C6 C5 170.2(2) . . . . ?
C7 O C6 C8 -67.4(3) . . . . ?
N1 C5 C6 O -65.1(3) . . . . ?
N1 C5 C6 C8 170.8(2) . . . . ?
C9 C8 C6 O -31.7(4) . . . . ?
C13 C8 C6 O 149.5(3) . . . . ?
C9 C8 C6 C5 88.2(3) . . . . ?
C13 C8 C6 C5 -90.6(3) . . . . ?
C3 N2 C1 N1 0.0(3) . . . . ?
C4 N2 C1 N1 -179.5(3) . . . . ?
C3 N2 C1 Au 176.1(2) . . . . ?
C4 N2 C1 Au -3.4(4) . . . . ?
C2 N1 C1 N2 0.6(3) . . . . ?
C5 N1 C1 N2 175.7(2) . . . . ?
C2 N1 C1 Au -175.5(2) . . . . ?
C5 N1 C1 Au -0.4(4) . . . . ?
N2 C3 C2 N1 1.0(3) . . . . ?
C1 N1 C2 C3 -1.0(3) . . . . ?
C5 N1 C2 C3 -176.1(3) . . . . ?
C8 C13 C12 C11 0.0(5) . . . . ?
C9 C10 C11 C12 0.1(5) . . . . ?
C13 C12 C11 C10 -0.2(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
C5 H5B Cl 0.97 2.95 3.822(3) 150.6 2_556
C4 H4B Cl 0.96 2.99 3.837(4) 148.1 4_666
C4 H4C Cl 0.96 2.97 3.818(4) 147.7 3_657

_refine_diff_density_max         0.556
_refine_diff_density_min         -0.768
_refine_diff_density_rms         0.066

