# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_leung958
_database_code_depnum_ccdc_archive 'CCDC 1534807'
_audit_update_record             
;
2017-02-27 deposited with the CCDC.
2017-05-03 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H18 As Au Cl N O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         611.69
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.8186(5)
_cell_length_b                   9.2688(5)
_cell_length_c                   10.8223(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.2433(18)
_cell_angle_gamma                90
_cell_volume                     972.11(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4863
_cell_measurement_theta_min      2.6011
_cell_measurement_theta_max      28.0849
_cell_measurement_temperature    103.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    2.090
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             580

_exptl_absorpt_coefficient_mu    9.407
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.16
_exptl_absorpt_correction_T_max  0.45

_exptl_special_details           
;
;

_diffrn_ambient_temperature      103.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Bruker KappaCCD'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            14442
_diffrn_reflns_av_R_equivalents  0.0664
_diffrn_reflns_av_unetI/netI     0.0698
_diffrn_reflns_theta_min         1.91
_diffrn_reflns_theta_max         27.99
_diffrn_reflns_theta_full        27.99
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14

_refine_special_details          
;
;

_reflns_number_total             3710
_reflns_number_gt                3401
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0348
_refine_ls_wR_factor_gt          0.0675
_refine_ls_wR_factor_ref         0.0706
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_number_reflns         3710
_refine_ls_number_parameters     235
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0198P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         2.361
_refine_diff_density_min         -2.019
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.005(13)

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'
As As 0.0499 2.0058 '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'

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2016)'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2016)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2016)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
As As1 0.21546(10) 0.89652(9) 0.32654(8) 0.00994(19) Uani d . . . 1 . .
Au Au1 0.26790(3) 0.65164(7) 0.32020(3) 0.01212(9) Uani d . . . 1 . .
C C1 0.0618(10) 0.9510(10) 0.2019(8) 0.0117(19) Uani d . . . 1 . .
C C2 -0.0354(11) 1.0486(12) 0.2286(9) 0.021(2) Uani d . . . 1 . .
H H2 -0.0256 1.0923 0.309 0.025 Uiso calc U . R 1 . .
C C3 -0.1486(11) 1.0830(12) 0.1374(9) 0.021(2) Uani d . . . 1 . .
H H3 -0.2145 1.1522 0.1546 0.025 Uiso calc U . R 1 . .
C C4 -0.1639(12) 1.0152(12) 0.0212(10) 0.023(2) Uani d . . . 1 . .
H H4 -0.2423 1.036 -0.0398 0.028 Uiso calc U . R 1 . .
C C5 -0.0669(10) 0.9182(14) -0.0063(9) 0.021(2) Uani d . . . 1 . .
H H5 -0.0775 0.8739 -0.0864 0.025 Uiso calc U . R 1 . .
C C6 0.0455(10) 0.8856(12) 0.0827(8) 0.019(2) Uani d . . . 1 . .
H H6 0.1125 0.8186 0.0638 0.022 Uiso calc U . R 1 . .
C C7 0.1719(10) 0.9704(11) 0.4806(8) 0.014(2) Uani d . . . 1 . .
C C8 0.1863(11) 1.1162(11) 0.5132(8) 0.019(2) Uani d . . . 1 . .
H H8 0.2269 1.1816 0.4622 0.022 Uiso calc U . R 1 . .
C C9 0.1404(9) 1.1644(17) 0.6217(7) 0.020(2) Uani d . . . 1 . .
H H9 0.1531 1.2625 0.6463 0.024 Uiso calc U . R 1 . .
C C10 0.0771(11) 1.0712(11) 0.6930(9) 0.018(2) Uani d . . . 1 . .
H H10 0.0428 1.1061 0.7646 0.021 Uiso calc U . R 1 . .
C C11 0.0630(10) 0.9275(11) 0.6617(8) 0.017(2) Uani d . . . 1 . .
H H11 0.0202 0.8634 0.7123 0.021 Uiso calc U . R 1 . .
C C12 0.1112(10) 0.8761(10) 0.5563(8) 0.015(2) Uani d . . . 1 . .
H H12 0.1029 0.7766 0.5357 0.018 Uiso calc U . R 1 . .
C C13 0.3215(10) 1.1202(10) 0.0747(8) 0.015(2) Uani d . . . 1 . .
H H13 0.2844 1.202 0.1106 0.018 Uiso calc U . R 1 . .
C C14 0.3188(11) 1.1156(11) -0.0527(9) 0.020(2) Uani d . . . 1 . .
H H14 0.2789 1.193 -0.1035 0.024 Uiso calc U . R 1 . .
C C15 0.3739(10) 0.9985(13) -0.1074(9) 0.020(2) Uani d . . . 1 . .
H H15 0.3731 0.9967 -0.1953 0.024 Uiso calc U . R 1 . .
C C16 0.4302(10) 0.8839(13) -0.0335(9) 0.024(2) Uani d . . . 1 . .
H H16 0.4673 0.803 -0.0706 0.029 Uiso calc U . R 1 . .
C C17 0.4320(10) 0.8886(12) 0.0976(8) 0.019(2) Uani d . . . 1 . .
H H17 0.4704 0.8106 0.1486 0.023 Uiso calc U . R 1 . .
C C18 0.3773(10) 1.0079(11) 0.1524(9) 0.015(2) Uani d . . . 1 . .
C C19 0.3720(9) 1.0151(10) 0.2904(9) 0.0119(19) Uani d . . . 1 . .
H H19 0.3553 1.1176 0.3128 0.014 Uiso calc U . R 1 . .
C C20 0.4987(10) 0.9615(11) 0.3755(9) 0.016(2) Uani d . . . 1 . .
H H20A 0.4794 0.9566 0.4624 0.019 Uiso calc U . R 1 . .
H H20B 0.5209 0.8628 0.3499 0.019 Uiso calc U . R 1 . .
Cl Cl1 0.3293(3) 0.4157(3) 0.3075(2) 0.0202(5) Uani d . . . 1 . .
N N1 0.6200(9) 1.0578(11) 0.3713(8) 0.022(2) Uani d . . . 1 . .
O O1 0.6011(10) 1.1845(9) 0.3506(11) 0.054(3) Uani d . . . 1 . .
O O2 0.7348(8) 1.0046(10) 0.3920(7) 0.0302(19) Uani d . . . 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
As1 C7 . 1.913(9) ?
As1 C1 . 1.923(9) ?
As1 C19 . 1.979(9) ?
As1 Au1 . 2.3309(11) ?
Au1 Cl1 . 2.279(3) ?
C1 C2 . 1.379(14) ?
C1 C6 . 1.410(12) ?
C2 C3 . 1.400(14) ?
C2 H2 . 0.95 ?
C3 C4 . 1.392(14) ?
C3 H3 . 0.95 ?
C4 C5 . 1.377(16) ?
C4 H4 . 0.95 ?
C5 C6 . 1.377(13) ?
C5 H5 . 0.95 ?
C6 H6 . 0.95 ?
C7 C12 . 1.395(13) ?
C7 C8 . 1.398(14) ?
C8 C9 . 1.397(12) ?
C8 H8 . 0.95 ?
C9 C10 . 1.372(16) ?
C9 H9 . 0.95 ?
C10 C11 . 1.376(14) ?
C10 H10 . 0.95 ?
C11 C12 . 1.388(12) ?
C11 H11 . 0.95 ?
C12 H12 . 0.95 ?
C13 C14 . 1.375(12) ?
C13 C18 . 1.394(13) ?
C13 H13 . 0.95 ?
C14 C15 . 1.387(15) ?
C14 H14 . 0.95 ?
C15 C16 . 1.391(15) ?
C15 H15 . 0.95 ?
C16 C17 . 1.416(13) ?
C16 H16 . 0.95 ?
C17 C18 . 1.402(14) ?
C17 H17 . 0.95 ?
C18 C19 . 1.504(12) ?
C19 C20 . 1.508(13) ?
C19 H19 . 1.0 ?
C20 N1 . 1.495(13) ?
C20 H20A . 0.99 ?
C20 H20B . 0.99 ?
N1 O1 . 1.205(14) ?
N1 O2 . 1.218(12) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 As1 C1 . . 104.9(4) ?
C7 As1 C19 . . 105.3(4) ?
C1 As1 C19 . . 105.2(4) ?
C7 As1 Au1 . . 117.1(3) ?
C1 As1 Au1 . . 112.8(3) ?
C19 As1 Au1 . . 110.7(3) ?
Cl1 Au1 As1 . . 176.63(7) ?
C2 C1 C6 . . 119.6(9) ?
C2 C1 As1 . . 121.1(7) ?
C6 C1 As1 . . 119.3(7) ?
C1 C2 C3 . . 119.9(9) ?
C1 C2 H2 . . 120.0 ?
C3 C2 H2 . . 120.0 ?
C4 C3 C2 . . 119.5(10) ?
C4 C3 H3 . . 120.3 ?
C2 C3 H3 . . 120.3 ?
C5 C4 C3 . . 120.8(10) ?
C5 C4 H4 . . 119.6 ?
C3 C4 H4 . . 119.6 ?
C4 C5 C6 . . 119.8(10) ?
C4 C5 H5 . . 120.1 ?
C6 C5 H5 . . 120.1 ?
C5 C6 C1 . . 120.3(10) ?
C5 C6 H6 . . 119.8 ?
C1 C6 H6 . . 119.8 ?
C12 C7 C8 . . 119.5(8) ?
C12 C7 As1 . . 117.7(7) ?
C8 C7 As1 . . 122.5(7) ?
C9 C8 C7 . . 119.2(10) ?
C9 C8 H8 . . 120.4 ?
C7 C8 H8 . . 120.4 ?
C10 C9 C8 . . 120.5(12) ?
C10 C9 H9 . . 119.8 ?
C8 C9 H9 . . 119.8 ?
C9 C10 C11 . . 120.5(10) ?
C9 C10 H10 . . 119.7 ?
C11 C10 H10 . . 119.7 ?
C10 C11 C12 . . 120.0(9) ?
C10 C11 H11 . . 120.0 ?
C12 C11 H11 . . 120.0 ?
C11 C12 C7 . . 120.2(9) ?
C11 C12 H12 . . 119.9 ?
C7 C12 H12 . . 119.9 ?
C14 C13 C18 . . 121.5(9) ?
C14 C13 H13 . . 119.2 ?
C18 C13 H13 . . 119.2 ?
C13 C14 C15 . . 120.4(9) ?
C13 C14 H14 . . 119.8 ?
C15 C14 H14 . . 119.8 ?
C14 C15 C16 . . 119.9(9) ?
C14 C15 H15 . . 120.0 ?
C16 C15 H15 . . 120.0 ?
C15 C16 C17 . . 119.5(10) ?
C15 C16 H16 . . 120.3 ?
C17 C16 H16 . . 120.3 ?
C18 C17 C16 . . 120.3(10) ?
C18 C17 H17 . . 119.9 ?
C16 C17 H17 . . 119.9 ?
C13 C18 C17 . . 118.3(9) ?
C13 C18 C19 . . 119.5(9) ?
C17 C18 C19 . . 122.1(9) ?
C18 C19 C20 . . 115.8(8) ?
C18 C19 As1 . . 108.9(6) ?
C20 C19 As1 . . 106.7(6) ?
C18 C19 H19 . . 108.4 ?
C20 C19 H19 . . 108.4 ?
As1 C19 H19 . . 108.4 ?
N1 C20 C19 . . 111.5(8) ?
N1 C20 H20A . . 109.3 ?
C19 C20 H20A . . 109.3 ?
N1 C20 H20B . . 109.3 ?
C19 C20 H20B . . 109.3 ?
H20A C20 H20B . . 108.0 ?
O1 N1 O2 . . 122.6(11) ?
O1 N1 C20 . . 119.3(10) ?
O2 N1 C20 . . 118.1(10) ?

