# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_h040811_0m
_database_code_depnum_ccdc_archive 'CCDC 1470874'
_audit_update_record             
;
2016-03-27 deposited with the CCDC.
2017-06-15 downloaded from the CCDC.
;
_audit_creation_date             2016-03-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            'Benzylthiazolium pyrophosphate'
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H17 N O7 P2 S'
_chemical_formula_sum            'C13 H17 N O7 P2 S'
_chemical_formula_weight         393.27
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.6460(6)
_cell_length_b                   8.5134(8)
_cell_length_c                   12.6646(11)
_cell_angle_alpha                85.150(3)
_cell_angle_beta                 83.269(3)
_cell_angle_gamma                87.675(3)
_cell_volume                     815.38(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6251
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      27.55
_cell_measurement_theta_min      2.40
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.934
_exptl_absorpt_coefficient_mu    0.432
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0472 before and 0.0390 after correction.
The Ratio of minimum to maximum transmission is 0.9378.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.035
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13597
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.557
_diffrn_reflns_theta_min         2.684
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 8.33
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       'kappa-stage diffractometer'
_diffrn_measurement_device_type  'Bruker/Nonius Kappa Apex2'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3225
_reflns_number_total             3718
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.451
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         3718
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0378
_refine_ls_restrained_S_all      1.103
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0279P)²+1.2118P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0878
_refine_ls_wR_factor_ref         0.0912
_refine_special_details          
;
O-H protons detected on Fourier difmap, but refined
using distance restraints (angles free).
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O24-H24 = O23-H23
 0.91 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C14(H14A,H14B), C15(H15A,H15B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12)
3.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.26469(7) 0.14963(7) 0.61944(4) 0.01411(13) Uani 1 1 d . . . . .
P17 P 0.77221(7) 0.29813(7) 0.48882(4) 0.01123(13) Uani 1 1 d . . . . .
P21 P 0.69368(7) 0.50150(7) 0.66462(4) 0.01082(13) Uani 1 1 d . . . . .
O16 O 0.69696(19) 0.12852(18) 0.52380(12) 0.0139(3) Uani 1 1 d . . . . .
O18 O 0.7313(2) 0.3382(2) 0.37805(12) 0.0172(3) Uani 1 1 d . . . . .
O19 O 0.95790(19) 0.30559(19) 0.51192(12) 0.0157(3) Uani 1 1 d . . . . .
O20 O 0.65031(19) 0.40687(18) 0.56709(12) 0.0156(3) Uani 1 1 d . . . . .
O22 O 0.8018(2) 0.40716(19) 0.73618(12) 0.0169(3) Uani 1 1 d . . . . .
O23 O 0.7697(2) 0.65879(18) 0.61393(12) 0.0146(3) Uani 1 1 d D . . . .
H23 H 0.872(3) 0.663(3) 0.5713(19) 0.022 Uiso 1 1 d DR . . . .
O24 O 0.51029(19) 0.54380(19) 0.72050(12) 0.0147(3) Uani 1 1 d D . . . .
H24 H 0.430(3) 0.585(3) 0.6767(19) 0.022 Uiso 1 1 d DR . . . .
N3 N 0.2536(2) 0.2851(2) 0.78731(14) 0.0120(4) Uani 1 1 d . . . . .
C2 C 0.1724(3) 0.2822(3) 0.70153(17) 0.0133(4) Uani 1 1 d . . . . .
H2 H 0.0728 0.3477 0.6876 0.016 Uiso 1 1 calc R . . . .
C4 C 0.3974(3) 0.1793(3) 0.79130(17) 0.0125(4) Uani 1 1 d . . . . .
C5 C 0.4207(3) 0.0948(3) 0.70443(17) 0.0128(4) Uani 1 1 d . . . . .
C6 C 0.1956(3) 0.3942(3) 0.87081(17) 0.0151(4) Uani 1 1 d . . . . .
H6A H 0.1166 0.4778 0.8417 0.018 Uiso 1 1 calc R . . . .
H6B H 0.2997 0.4454 0.8906 0.018 Uiso 1 1 calc R . . . .
C7 C 0.1000(3) 0.3100(3) 0.96918(17) 0.0138(4) Uani 1 1 d . . . . .
C8 C 0.1612(3) 0.3138(3) 1.06795(18) 0.0180(5) Uani 1 1 d . . . . .
H8 H 0.2671 0.3657 1.0732 0.022 Uiso 1 1 calc R . . . .
C9 C 0.0689(3) 0.2422(3) 1.15900(18) 0.0197(5) Uani 1 1 d . . . . .
H9 H 0.1115 0.2451 1.2263 0.024 Uiso 1 1 calc R . . . .
C10 C -0.0854(3) 0.1666(3) 1.15158(19) 0.0219(5) Uani 1 1 d . . . . .
H10 H -0.1491 0.1177 1.2138 0.026 Uiso 1 1 calc R . . . .
C11 C -0.1467(3) 0.1624(3) 1.0536(2) 0.0270(6) Uani 1 1 d . . . . .
H11 H -0.2525 0.1101 1.0486 0.032 Uiso 1 1 calc R . . . .
C12 C -0.0548(3) 0.2342(3) 0.96256(19) 0.0208(5) Uani 1 1 d . . . . .
H12 H -0.0980 0.2313 0.8955 0.025 Uiso 1 1 calc R . . . .
C13 C 0.5080(3) 0.1733(3) 0.88096(17) 0.0161(5) Uani 1 1 d . . . . .
H13A H 0.5709 0.2720 0.8778 0.024 Uiso 1 1 calc GR . . . .
H13B H 0.5934 0.0846 0.8751 0.024 Uiso 1 1 calc GR . . . .
H13C H 0.4326 0.1595 0.9490 0.024 Uiso 1 1 calc GR . . . .
C14 C 0.5628(3) -0.0262(3) 0.67649(18) 0.0139(4) Uani 1 1 d . . . . .
H14A H 0.5212 -0.0966 0.6270 0.017 Uiso 1 1 calc R . . . .
H14B H 0.5867 -0.0913 0.7421 0.017 Uiso 1 1 calc R . . . .
C15 C 0.7328(3) 0.0482(3) 0.62479(17) 0.0144(4) Uani 1 1 d . . . . .
H15A H 0.7723 0.1241 0.6714 0.017 Uiso 1 1 calc R . . . .
H15B H 0.8266 -0.0341 0.6132 0.017 Uiso 1 1 calc R . . . .


_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
S1 C2 1.678(2) . ?
S1 C5 1.723(2) . ?
P17 O16 1.5849(16) . ?
P17 O18 1.4816(16) . ?
P17 O19 1.4877(16) . ?
P17 O20 1.6053(16) . ?
P21 O20 1.6032(16) . ?
P21 O22 1.4657(16) . ?
P21 O23 1.5405(16) . ?
P21 O24 1.5383(15) . ?
O16 C15 1.448(3) . ?
O23 H23 0.895(17) . ?
O24 H24 0.916(17) . ?
N3 C2 1.315(3) . ?
N3 C4 1.395(3) . ?
N3 C6 1.483(3) . ?
C2 H2 0.9500 . ?
C4 C5 1.356(3) . ?
C4 C13 1.490(3) . ?
C5 C14 1.499(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.509(3) . ?
C7 C8 1.389(3) . ?
C7 C12 1.385(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.387(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.383(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.380(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.387(3) . ?
C12 H12 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.522(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?

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
C2 S1 C5 91.24(11) . . ?
O16 P17 O20 102.02(8) . . ?
O18 P17 O16 106.35(9) . . ?
O18 P17 O19 118.67(9) . . ?
O18 P17 O20 108.95(9) . . ?
O19 P17 O16 110.95(9) . . ?
O19 P17 O20 108.61(9) . . ?
O22 P21 O20 112.39(9) . . ?
O22 P21 O23 116.44(9) . . ?
O22 P21 O24 112.14(9) . . ?
O23 P21 O20 105.76(9) . . ?
O24 P21 O20 103.33(9) . . ?
O24 P21 O23 105.67(9) . . ?
C15 O16 P17 119.85(13) . . ?
P21 O20 P17 131.67(10) . . ?
P21 O23 H23 122.1(18) . . ?
P21 O24 H24 115.7(17) . . ?
C2 N3 C4 114.26(18) . . ?
C2 N3 C6 121.76(18) . . ?
C4 N3 C6 123.97(18) . . ?
S1 C2 H2 123.8 . . ?
N3 C2 S1 112.35(16) . . ?
N3 C2 H2 123.8 . . ?
N3 C4 C13 120.8(2) . . ?
C5 C4 N3 111.40(19) . . ?
C5 C4 C13 127.7(2) . . ?
C4 C5 S1 110.74(16) . . ?
C4 C5 C14 128.1(2) . . ?
C14 C5 S1 121.07(17) . . ?
N3 C6 H6A 109.2 . . ?
N3 C6 H6B 109.2 . . ?
N3 C6 C7 112.04(18) . . ?
H6A C6 H6B 107.9 . . ?
C7 C6 H6A 109.2 . . ?
C7 C6 H6B 109.2 . . ?
C8 C7 C6 120.6(2) . . ?
C12 C7 C6 120.1(2) . . ?
C12 C7 C8 119.2(2) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 C7 120.5(2) . . ?
C9 C8 H8 119.7 . . ?
C8 C9 H9 120.1 . . ?
C10 C9 C8 119.8(2) . . ?
C10 C9 H9 120.1 . . ?
C9 C10 H10 120.1 . . ?
C11 C10 C9 119.9(2) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.4(2) . . ?
C12 C11 H11 119.8 . . ?
C7 C12 C11 120.2(2) . . ?
C7 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C4 C13 H13A 109.5 . . ?
C4 C13 H13B 109.5 . . ?
C4 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C5 C14 H14A 109.1 . . ?
C5 C14 H14B 109.1 . . ?
C5 C14 C15 112.31(18) . . ?
H14A C14 H14B 107.9 . . ?
C15 C14 H14A 109.1 . . ?
C15 C14 H14B 109.1 . . ?
O16 C15 C14 107.53(17) . . ?
O16 C15 H15A 110.2 . . ?
O16 C15 H15B 110.2 . . ?
C14 C15 H15A 110.2 . . ?
C14 C15 H15B 110.2 . . ?
H15A C15 H15B 108.5 . . ?

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
S1 C5 C14 C15 95.5(2) . . . . ?
P17 O16 C15 C14 137.32(15) . . . . ?
O16 P17 O20 P21 111.49(14) . . . . ?
O18 P17 O16 C15 173.36(14) . . . . ?
O18 P17 O20 P21 -136.34(14) . . . . ?
O19 P17 O16 C15 43.00(17) . . . . ?
O19 P17 O20 P21 -5.73(17) . . . . ?
O20 P17 O16 C15 -72.52(15) . . . . ?
O22 P21 O20 P17 -44.99(17) . . . . ?
O23 P21 O20 P17 83.09(15) . . . . ?
O24 P21 O20 P17 -166.10(13) . . . . ?
N3 C4 C5 S1 0.4(2) . . . . ?
N3 C4 C5 C14 177.7(2) . . . . ?
N3 C6 C7 C8 121.6(2) . . . . ?
N3 C6 C7 C12 -61.4(3) . . . . ?
C2 S1 C5 C4 -0.26(17) . . . . ?
C2 S1 C5 C14 -177.74(18) . . . . ?
C2 N3 C4 C5 -0.4(3) . . . . ?
C2 N3 C4 C13 177.26(19) . . . . ?
C2 N3 C6 C7 105.0(2) . . . . ?
C4 N3 C2 S1 0.2(2) . . . . ?
C4 N3 C6 C7 -75.7(2) . . . . ?
C4 C5 C14 C15 -81.5(3) . . . . ?
C5 S1 C2 N3 0.01(17) . . . . ?
C5 C14 C15 O16 -64.8(2) . . . . ?
C6 N3 C2 S1 179.59(15) . . . . ?
C6 N3 C4 C5 -179.77(18) . . . . ?
C6 N3 C4 C13 -2.1(3) . . . . ?
C6 C7 C8 C9 177.1(2) . . . . ?
C6 C7 C12 C11 -177.3(2) . . . . ?
C7 C8 C9 C10 -0.1(4) . . . . ?
C8 C7 C12 C11 -0.2(4) . . . . ?
C8 C9 C10 C11 0.1(4) . . . . ?
C9 C10 C11 C12 -0.3(4) . . . . ?
C10 C11 C12 C7 0.3(4) . . . . ?
C12 C7 C8 C9 0.1(3) . . . . ?
C13 C4 C5 S1 -177.07(18) . . . . ?
C13 C4 C5 C14 0.2(4) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_original_sample_id h040811
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method 'acetone water'
####################################################################### 
# 
# 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_h200316_1_1_0m
_database_code_depnum_ccdc_archive 'CCDC 1470873'
_audit_update_record             
;
2016-03-27 deposited with the CCDC.
2017-06-15 downloaded from the CCDC.
;
_audit_creation_date             2016-03-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            'Benzylthiazolium-gold(I) chloride'
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H15 Au Cl N O S'
_chemical_formula_sum            'C13 H15 Au Cl N O S'
_chemical_formula_weight         465.74
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.7017(7)
_cell_length_b                   8.8040(7)
_cell_length_c                   10.7083(9)
_cell_angle_alpha                108.863(3)
_cell_angle_beta                 91.805(3)
_cell_angle_gamma                114.116(3)
_cell_volume                     695.72(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9855
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      30.58
_cell_measurement_theta_min      2.61
_shelx_estimated_absorpt_T_max   0.772
_shelx_estimated_absorpt_T_min   0.355
_exptl_absorpt_coefficient_mu    10.901
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5311
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1166 before and 0.0352 after correction.
The Ratio of minimum to maximum transmission is 0.7118.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.223
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             440
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.025
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            22080
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.603
_diffrn_reflns_theta_min         2.612
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 8.33
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device       'kappa-stage diffractometer'
_diffrn_measurement_device_type  'Bruker/Nonius Kappa Apex2'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'double mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms high brilliance'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4045
_reflns_number_total             4232
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         2.237
_refine_diff_density_min         -1.366
_refine_diff_density_rms         0.136
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         4232
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0182
_refine_ls_R_factor_gt           0.0166
_refine_ls_restrained_S_all      1.112
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0244P)²+0.4311P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0421
_refine_ls_wR_factor_ref         0.0428
_refine_special_details          
'OH proton refined using distance restraint (free angle).'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O1-H1
 0.91 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C7(H7A,H7B), C5(H5A,H5B)
3.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C11(H11), C10(H10), C13(H13), C12(H12)
3.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_special_details      
;
The structure was solved using Patterson Methods, followed by a Tangent Expansion (ShelXS). RE = 0.3, Nqual =  -1, Ralpha = 0.025
;
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 0.55050(2) 0.26866(2) 0.40103(2) 0.01177(3) Uani 1 1 d . . . . .
Cl1 Cl 0.47921(8) 0.14490(8) 0.17159(6) 0.01758(11) Uani 1 1 d . . . . .
S1 S 0.79136(7) 0.57745(8) 0.68000(6) 0.01392(10) Uani 1 1 d . . . . .
O1 O 1.1308(3) 0.8070(3) 0.8607(2) 0.0250(4) Uani 1 1 d D . . . .
H1 H 1.237(3) 0.821(5) 0.860(4) 0.037 Uiso 1 1 d DR . . . .
N1 N 0.5523(2) 0.3064(3) 0.68948(19) 0.0116(3) Uani 1 1 d . . . . .
C3 C 0.7676(3) 0.5666(3) 0.8371(2) 0.0137(4) Uani 1 1 d . . . . .
C2 C 0.6323(3) 0.4101(3) 0.8248(2) 0.0127(4) Uani 1 1 d . . . . .
C4 C 0.8854(3) 0.7156(4) 0.9631(3) 0.0183(5) Uani 1 1 d . . . . .
H4A H 0.8468 0.6860 1.0419 0.022 Uiso 1 1 calc R . . . .
H4B H 0.8773 0.8269 0.9702 0.022 Uiso 1 1 calc R . . . .
C7 C 0.3934(3) 0.1384(3) 0.6513(2) 0.0129(4) Uani 1 1 d . . . . .
H7A H 0.4019 0.0710 0.7073 0.015 Uiso 1 1 calc R . . . .
H7B H 0.3815 0.0642 0.5563 0.015 Uiso 1 1 calc R . . . .
C9 C 0.0844(3) 0.0278(3) 0.6699(2) 0.0151(4) Uani 1 1 d . . . . .
H9 H 0.0847 -0.0814 0.6660 0.018 Uiso 1 1 calc R . . . .
C6 C 0.5683(3) 0.3381(3) 0.9315(2) 0.0168(4) Uani 1 1 d . . . . .
H6A H 0.4458 0.3066 0.9259 0.025 Uiso 1 1 calc GR . . . .
H6B H 0.6315 0.4293 1.0201 0.025 Uiso 1 1 calc GR . . . .
H6C H 0.5857 0.2312 0.9185 0.025 Uiso 1 1 calc GR . . . .
C1 C 0.6200(3) 0.3762(3) 0.5993(2) 0.0121(4) Uani 1 1 d . . . . .
C11 C -0.0674(3) 0.2066(4) 0.6841(3) 0.0198(5) Uani 1 1 d . . . . .
H11 H -0.1708 0.2190 0.6893 0.024 Uiso 1 1 calc R . . . .
C5 C 1.0726(3) 0.7490(4) 0.9672(3) 0.0195(5) Uani 1 1 d . . . . .
H5A H 1.1435 0.8416 1.0545 0.023 Uiso 1 1 calc R . . . .
H5B H 1.0824 0.6375 0.9566 0.023 Uiso 1 1 calc R . . . .
C10 C -0.0655(3) 0.0472(3) 0.6775(2) 0.0182(5) Uani 1 1 d . . . . .
H10 H -0.1680 -0.0494 0.6782 0.022 Uiso 1 1 calc R . . . .
C8 C 0.2353(3) 0.1691(3) 0.6680(2) 0.0113(4) Uani 1 1 d . . . . .
C13 C 0.2337(3) 0.3288(3) 0.6758(3) 0.0162(4) Uani 1 1 d . . . . .
H13 H 0.3364 0.4258 0.6761 0.019 Uiso 1 1 calc R . . . .
C12 C 0.0825(3) 0.3481(4) 0.6833(3) 0.0201(5) Uani 1 1 d . . . . .
H12 H 0.0819 0.4574 0.6877 0.024 Uiso 1 1 calc R . . . .


_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 Cl1 2.2867(6) . ?
Au1 C1 1.980(2) . ?
S1 C3 1.730(2) . ?
S1 C1 1.697(2) . ?
O1 H1 0.881(19) . ?
O1 C5 1.421(3) . ?
N1 C2 1.407(3) . ?
N1 C7 1.473(3) . ?
N1 C1 1.334(3) . ?
C3 C2 1.360(3) . ?
C3 C4 1.504(3) . ?
C2 C6 1.496(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.529(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.513(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.384(3) . ?
C9 C8 1.398(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C11 H11 0.9500 . ?
C11 C10 1.390(4) . ?
C11 C12 1.391(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C10 H10 0.9500 . ?
C8 C13 1.387(3) . ?
C13 H13 0.9500 . ?
C13 C12 1.396(3) . ?
C12 H12 0.9500 . ?

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 178.06(6) . . ?
C1 S1 C3 93.38(12) . . ?
C5 O1 H1 109(3) . . ?
C2 N1 C7 121.5(2) . . ?
C1 N1 C2 116.28(19) . . ?
C1 N1 C7 121.97(19) . . ?
C2 C3 S1 109.81(17) . . ?
C2 C3 C4 128.5(2) . . ?
C4 C3 S1 121.66(19) . . ?
N1 C2 C6 119.6(2) . . ?
C3 C2 N1 111.4(2) . . ?
C3 C2 C6 129.0(2) . . ?
C3 C4 H4A 109.0 . . ?
C3 C4 H4B 109.0 . . ?
C3 C4 C5 113.1(2) . . ?
H4A C4 H4B 107.8 . . ?
C5 C4 H4A 109.0 . . ?
C5 C4 H4B 109.0 . . ?
N1 C7 H7A 109.0 . . ?
N1 C7 H7B 109.0 . . ?
N1 C7 C8 112.74(18) . . ?
H7A C7 H7B 107.8 . . ?
C8 C7 H7A 109.0 . . ?
C8 C7 H7B 109.0 . . ?
C10 C9 H9 120.0 . . ?
C10 C9 C8 120.0(2) . . ?
C8 C9 H9 120.0 . . ?
C2 C6 H6A 109.5 . . ?
C2 C6 H6B 109.5 . . ?
C2 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
S1 C1 Au1 122.43(13) . . ?
N1 C1 Au1 128.34(17) . . ?
N1 C1 S1 109.16(17) . . ?
C10 C11 H11 120.1 . . ?
C10 C11 C12 119.8(2) . . ?
C12 C11 H11 120.1 . . ?
O1 C5 C4 108.3(2) . . ?
O1 C5 H5A 110.0 . . ?
O1 C5 H5B 110.0 . . ?
C4 C5 H5A 110.0 . . ?
C4 C5 H5B 110.0 . . ?
H5A C5 H5B 108.4 . . ?
C9 C10 C11 120.6(2) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C9 C8 C7 118.2(2) . . ?
C13 C8 C7 122.3(2) . . ?
C13 C8 C9 119.5(2) . . ?
C8 C13 H13 119.7 . . ?
C8 C13 C12 120.5(2) . . ?
C12 C13 H13 119.7 . . ?
C11 C12 C13 119.7(2) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?

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
S1 C3 C2 N1 -0.7(2) . . . . ?
S1 C3 C2 C6 176.7(2) . . . . ?
S1 C3 C4 C5 -61.4(3) . . . . ?
N1 C7 C8 C9 -163.4(2) . . . . ?
N1 C7 C8 C13 19.4(3) . . . . ?
C3 S1 C1 Au1 -177.88(14) . . . . ?
C3 S1 C1 N1 -0.80(18) . . . . ?
C3 C4 C5 O1 63.9(3) . . . . ?
C2 N1 C7 C8 79.9(3) . . . . ?
C2 N1 C1 Au1 177.42(16) . . . . ?
C2 N1 C1 S1 0.6(2) . . . . ?
C2 C3 C4 C5 118.9(3) . . . . ?
C4 C3 C2 N1 179.1(2) . . . . ?
C4 C3 C2 C6 -3.5(4) . . . . ?
C7 N1 C2 C3 -174.5(2) . . . . ?
C7 N1 C2 C6 7.8(3) . . . . ?
C7 N1 C1 Au1 -8.0(3) . . . . ?
C7 N1 C1 S1 175.13(16) . . . . ?
C7 C8 C13 C12 176.2(2) . . . . ?
C9 C8 C13 C12 -1.0(4) . . . . ?
C1 S1 C3 C2 0.86(19) . . . . ?
C1 S1 C3 C4 -179.0(2) . . . . ?
C1 N1 C2 C3 0.1(3) . . . . ?
C1 N1 C2 C6 -177.6(2) . . . . ?
C1 N1 C7 C8 -94.4(2) . . . . ?
C10 C9 C8 C7 -176.4(2) . . . . ?
C10 C9 C8 C13 0.9(3) . . . . ?
C10 C11 C12 C13 0.0(4) . . . . ?
C8 C9 C10 C11 -0.4(4) . . . . ?
C8 C13 C12 C11 0.6(4) . . . . ?
C12 C11 C10 C9 -0.1(4) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2016-03-22
_olex2_date_sample_submission    2016-03-15
_olex2_submission_original_sample_id h200316_1_1
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method 'pentane ethylacetate'
