# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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 1978213'
loop_
_audit_author_name
_audit_author_address
'Miquel Barcelo-Oliver'
;University of the Balearic Islands
Spain
;
_audit_update_record             
;
2020-01-16 deposited with the CCDC.	2020-02-17 downloaded from the CCDC.
;

_audit_creation_date             2019-04-03T20:29:04-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C10 H17 Au Cl3 N3 O'
_chemical_formula_sum            'C10 H17 Au Cl3 N3 O'
_chemical_formula_weight         498.59

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.0041(19)
_cell_length_b                   15.654(4)
_cell_length_c                   16.326(4)
_cell_angle_alpha                90
_cell_angle_beta                 115.405(8)
_cell_angle_gamma                90
_cell_volume                     1617.0(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    2167
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      24.67
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_exptl_crystal_density_diffrn    2.048
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             944

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    9.586
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS - Bruker/Siemens area detector absorption and other corrections -
;
_exptl_absorpt_correction_T_min  0.628
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.25
_shelx_estimated_absorpt_T_max   0.553

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'sealed x-ray tube'
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'APEX-II CCD'
_diffrn_orient_matrix_ub_11      0.066788
_diffrn_orient_matrix_ub_12      -0.011395
_diffrn_orient_matrix_ub_13      0.009682
_diffrn_orient_matrix_ub_21      -0.000194
_diffrn_orient_matrix_ub_22      -0.127698
_diffrn_orient_matrix_ub_23      -0.02857
_diffrn_orient_matrix_ub_31      0.011718
_diffrn_orient_matrix_ub_32      0.062832
_diffrn_orient_matrix_ub_33      -0.056309
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'φ or ω oscillation scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0687
_diffrn_reflns_av_unetI/netI     0.1283
_diffrn_reflns_number            7301
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.897
_diffrn_reflns_theta_max         28.508
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.939
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.939
_reflns_Friedel_coverage         0
_reflns_number_total             3861
_reflns_number_gt                2029
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 software'
_computing_cell_refinement       'SAINT V6.28A integration software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2017/1
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0002P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3861
_refine_ls_number_parameters     164
_refine_ls_number_restraints     46
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1145
_refine_ls_R_factor_gt           0.0516
_refine_ls_wR_factor_ref         0.1136
_refine_ls_wR_factor_gt          0.0975
_refine_ls_goodness_of_fit_ref   0.88
_refine_ls_restrained_S_all      0.897
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.969
_refine_diff_density_min         -1.958
_refine_diff_density_rms         0.16

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.54908(5) 0.62253(3) 0.45414(3) 0.06185(17) Uani 1 1 d . . . . .
Cl1 Cl 0.7967(4) 0.55229(19) 0.5764(2) 0.0796(8) Uani 1 1 d . . . . .
Cl2 Cl 0.6295(5) 0.5408(2) 0.3595(2) 0.0875(9) Uani 1 1 d . . . . .
Cl3 Cl 0.2995(4) 0.6927(2) 0.3359(2) 0.0878(9) Uani 1 1 d . . . . .
N1 N 0.6229(11) 0.8222(6) 0.6341(6) 0.069(2) Uani 1 1 d . . . . .
C2 C 0.6457(14) 0.7623(7) 0.5764(7) 0.065(3) Uani 1 1 d . . . . .
O2 O 0.7998(9) 0.7627(4) 0.5593(5) 0.076(2) Uani 1 1 d . . . . .
N3 N 0.4910(10) 0.7018(5) 0.5385(5) 0.061(2) Uani 1 1 d . . . . .
C4 C 0.3179(14) 0.7012(8) 0.5554(7) 0.068(3) Uani 1 1 d . . . . .
N4 N 0.1693(12) 0.6427(6) 0.5151(6) 0.086(3) Uani 1 1 d . . . . .
H4A H 0.18397 0.60603 0.478968 0.103 Uiso 1 1 calc R U . . .
H4B H 0.058388 0.641474 0.525143 0.103 Uiso 1 1 calc R U . . .
C5 C 0.2900(14) 0.7636(8) 0.6108(7) 0.083(4) Uani 1 1 d . . . . .
H5 H 0.168103 0.766098 0.620074 0.1 Uiso 1 1 calc R U . . .
C6 C 0.4488(15) 0.8198(9) 0.6498(8) 0.089(4) Uani 1 1 d . . . . .
H6 H 0.43796 0.85943 0.690058 0.107 Uiso 1 1 calc R U . . .
C7 C 0.7828(15) 0.8897(7) 0.6730(8) 0.081(4) Uani 1 1 d D . . . .
H7A H 0.786608 0.907565 0.730526 0.097 Uiso 1 1 calc R U . . .
H7B H 0.920542 0.866441 0.684733 0.097 Uiso 1 1 calc R U . . .
C8 C 0.744(2) 0.9632(9) 0.6150(10) 0.125(5) Uani 1 1 d D U . . .
H8A H 0.612118 0.990167 0.607282 0.15 Uiso 1 1 calc R U . . .
H8B H 0.729981 0.945613 0.555828 0.15 Uiso 1 1 calc R U . . .
C9 C 0.926(3) 1.0274(12) 0.6570(13) 0.203(8) Uani 1 1 d D U . . .
H9A H 0.900416 1.058303 0.702735 0.243 Uiso 1 1 calc R U . . .
H9B H 1.052296 0.9934 0.689513 0.243 Uiso 1 1 calc R U . . .
C10 C 0.981(4) 1.0862(15) 0.6118(17) 0.271(12) Uani 1 1 d D U . . .
H10A H 0.85283 1.116504 0.573078 0.326 Uiso 1 1 calc R U . . .
H10B H 1.028828 1.056091 0.572254 0.326 Uiso 1 1 calc R U . . .
C11 C 1.149(3) 1.1537(12) 0.6637(16) 0.212(10) Uani 1 1 d D U . . .
H11A H 1.113584 1.208087 0.632375 0.255 Uiso 1 1 calc R U . . .
H11B H 1.15897 1.161343 0.724448 0.255 Uiso 1 1 calc R U . . .
C12 C 1.332(3) 1.1233(13) 0.6670(18) 0.249(12) Uani 1 1 d D U . . .
H12A H 1.368108 1.070969 0.700868 0.374 Uiso 1 1 calc R U . . .
H12B H 1.44226 1.164545 0.695967 0.374 Uiso 1 1 calc R U . . .
H12C H 1.316599 1.112924 0.606514 0.374 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 N3 2.021(8) . ?
Au1 Cl2 2.256(3) . ?
Au1 Cl3 2.257(3) . ?
Au1 Cl1 2.287(3) . ?
N1 C6 1.350(11) . ?
N1 C2 1.386(12) . ?
N1 C7 1.471(12) . ?
C2 O2 1.225(10) . ?
C2 N3 1.370(11) . ?
N3 C4 1.354(10) . ?
C4 N4 1.329(12) . ?
C4 C5 1.401(14) . ?
N4 H4A 0.86 . ?
N4 H4B 0.86 . ?
C5 C6 1.345(14) . ?
C5 H5 0.93 . ?
C6 H6 0.93 . ?
C7 C8 1.439(13) . ?
C7 H7A 0.97 . ?
C7 H7B 0.97 . ?
C8 C9 1.538(14) . ?
C8 H8A 0.97 . ?
C8 H8B 0.97 . ?
C9 C10 1.332(16) . ?
C9 H9A 0.97 . ?
C9 H9B 0.97 . ?
C10 C11 1.538(16) . ?
C10 H10A 0.97 . ?
C10 H10B 0.97 . ?
C11 C12 1.349(16) . ?
C11 H11A 0.97 . ?
C11 H11B 0.97 . ?
C12 H12A 0.96 . ?
C12 H12B 0.96 . ?
C12 H12C 0.96 . ?

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
N3 Au1 Cl2 176.1(2) . . ?
N3 Au1 Cl3 88.6(2) . . ?
Cl2 Au1 Cl3 91.09(12) . . ?
N3 Au1 Cl1 90.0(2) . . ?
Cl2 Au1 Cl1 90.39(11) . . ?
Cl3 Au1 Cl1 178.34(10) . . ?
C6 N1 C2 119.1(9) . . ?
C6 N1 C7 121.4(9) . . ?
C2 N1 C7 119.4(8) . . ?
O2 C2 N3 120.2(10) . . ?
O2 C2 N1 121.4(9) . . ?
N3 C2 N1 118.4(8) . . ?
C4 N3 C2 121.1(9) . . ?
C4 N3 Au1 126.4(7) . . ?
C2 N3 Au1 112.4(6) . . ?
N4 C4 N3 118.9(11) . . ?
N4 C4 C5 120.3(9) . . ?
N3 C4 C5 120.7(10) . . ?
C4 N4 H4A 120 . . ?
C4 N4 H4B 120 . . ?
H4A N4 H4B 120 . . ?
C6 C5 C4 116.5(10) . . ?
C6 C5 H5 121.7 . . ?
C4 C5 H5 121.7 . . ?
C5 C6 N1 124.0(11) . . ?
C5 C6 H6 118 . . ?
N1 C6 H6 118 . . ?
C8 C7 N1 113.3(10) . . ?
C8 C7 H7A 108.9 . . ?
N1 C7 H7A 108.9 . . ?
C8 C7 H7B 108.9 . . ?
N1 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
C7 C8 C9 110.0(12) . . ?
C7 C8 H8A 109.7 . . ?
C9 C8 H8A 109.7 . . ?
C7 C8 H8B 109.7 . . ?
C9 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
C10 C9 C8 125.8(17) . . ?
C10 C9 H9A 105.9 . . ?
C8 C9 H9A 105.9 . . ?
C10 C9 H9B 105.9 . . ?
C8 C9 H9B 105.9 . . ?
H9A C9 H9B 106.2 . . ?
C9 C10 C11 120(2) . . ?
C9 C10 H10A 107.3 . . ?
C11 C10 H10A 107.3 . . ?
C9 C10 H10B 107.3 . . ?
C11 C10 H10B 107.3 . . ?
H10A C10 H10B 106.9 . . ?
C12 C11 C10 105.7(19) . . ?
C12 C11 H11A 110.6 . . ?
C10 C11 H11A 110.6 . . ?
C12 C11 H11B 110.6 . . ?
C10 C11 H11B 110.6 . . ?
H11A C11 H11B 108.7 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
C6 N1 C2 O2 179.1(10) . . . . ?
C7 N1 C2 O2 2.3(15) . . . . ?
C6 N1 C2 N3 -1.0(15) . . . . ?
C7 N1 C2 N3 -177.8(9) . . . . ?
O2 C2 N3 C4 -178.9(9) . . . . ?
N1 C2 N3 C4 1.2(14) . . . . ?
O2 C2 N3 Au1 -1.6(12) . . . . ?
N1 C2 N3 Au1 178.5(7) . . . . ?
C2 N3 C4 N4 178.1(9) . . . . ?
Au1 N3 C4 N4 1.3(14) . . . . ?
C2 N3 C4 C5 1.3(15) . . . . ?
Au1 N3 C4 C5 -175.5(8) . . . . ?
N4 C4 C5 C6 179.3(10) . . . . ?
N3 C4 C5 C6 -3.9(16) . . . . ?
C4 C5 C6 N1 4.3(18) . . . . ?
C2 N1 C6 C5 -1.9(17) . . . . ?
C7 N1 C6 C5 174.8(11) . . . . ?
C6 N1 C7 C8 -90.6(14) . . . . ?
C2 N1 C7 C8 86.1(13) . . . . ?
N1 C7 C8 C9 -175.5(12) . . . . ?
C7 C8 C9 C10 156(2) . . . . ?
C8 C9 C10 C11 172.2(19) . . . . ?
C9 C10 C11 C12 96(3) . . . . ?

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
N4 H4A Cl1 0.86 2.66 3.451(10) 153.2 3_666 yes
N4 H4B Cl1 0.86 2.71 3.472(8) 149 1_455 yes
C5 H5 O2 0.93 2.33 3.166(11) 148.7 1_455 yes
C6 H6 Cl2 0.93 2.95 3.790(13) 150.8 4_576 yes
C7 H7B Cl3 0.97 2.89 3.684(11) 139.4 4_676 yes
C7 H7A Cl2 0.97 2.88 3.797(12) 158.4 4_576 yes



# END of CIF
