# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_and_1
_database_code_depnum_ccdc_archive 'CCDC 1835869'
_audit_update_record             
;
2018-04-09 deposited with the CCDC.
2018-06-14 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            'C8 H15 N2 Na O2 S2'
_chemical_formula_weight         258.33

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Na Na 0.0362 0.0249 '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        'I 2/a'
_space_group_name_Hall           '-I 2ya'

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

_cell_length_a                   15.2035(17)
_cell_length_b                   11.0876(11)
_cell_length_c                   15.0618(15)
_cell_angle_alpha                90
_cell_angle_beta                 111.081(13)
_cell_angle_gamma                90
_cell_volume                     2369.0(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    300.0(1)
_cell_measurement_reflns_used    1292
_cell_measurement_theta_min      3.9870
_cell_measurement_theta_max      28.3470

_exptl_crystal_description       Parallelepiped
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_F_000             1088
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.468
_shelx_estimated_absorpt_T_min   0.800
_shelx_estimated_absorpt_T_max   0.912
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.66852
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
crysalispro, agilent technologies, 
version 1.171.37.35 (release 13-08-2014 crysalis171 .net) 
(compiled aug 13 2014,18:06:01) 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300.0(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'enhance (mo) x-ray source'
_diffrn_measurement_device_type  'xcalibur, sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1048
_diffrn_reflns_number            5411
_diffrn_reflns_av_unetI/netI     0.0566
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.675
_diffrn_reflns_theta_max         29.001
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.858
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.858
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.858
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2706
_reflns_number_gt                1881
_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       
; 
crysalispro, agilent technologies, 
version 1.171.37.35 (release 13-08-2014 crysalis171 .net) 
(compiled aug 13 2014,18:06:01) 
;
_computing_cell_refinement       
; 
crysalispro, agilent technologies, 
version 1.171.37.35 (release 13-08-2014 crysalis171 .net) 
(compiled aug 13 2014,18:06:01) 
;
_computing_data_reduction        
; 
crysalispro, agilent technologies, 
version 1.171.37.35 (release 13-08-2014 crysalis171 .net) 
(compiled aug 13 2014,18:06:01) 
;
_computing_structure_solution    
'SHELXT - G.M.Sheldrick,Acta Crystallogr.A71(2015)3-8.'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'ORTEX - P. McArdle, J.Appl.Cryst.,1995,28,65-65.'
_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)+(0.0302P)²+1.5556P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2706
_refine_ls_number_parameters     149
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0840
_refine_ls_R_factor_gt           0.0500
_refine_ls_wR_factor_ref         0.1005
_refine_ls_wR_factor_gt          0.0873
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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
S1 S 0.35903(5) 0.39560(7) 0.15020(5) 0.0410(2) Uani 1 1 d . . . . .
S2 S 0.34355(5) 0.56465(7) 0.29553(5) 0.0439(2) Uani 1 1 d . . . . .
Na1 Na 0.81295(7) 0.14593(10) 0.61188(7) 0.0410(3) Uani 1 1 d . . . . .
O1 O 0.65016(11) 0.15870(18) 0.52491(11) 0.0410(5) Uani 1 1 d . . . . .
N1 N 0.35890(14) 0.3280(2) 0.31913(13) 0.0311(5) Uani 1 1 d . . . . .
O2 O 0.82381(17) 0.3563(2) 0.64084(17) 0.0585(6) Uani 1 1 d . . . . .
N2 N 0.5827(2) 0.1358(3) 0.63289(17) 0.0437(7) Uani 1 1 d . . . . .
C1 C 0.35434(18) 0.3396(3) 0.41411(17) 0.0372(6) Uani 1 1 d . . . . .
H1A H 0.3060 0.2862 0.4196 0.048 Uiso 1 1 calc R U . . .
H1B H 0.3374 0.4216 0.4236 0.048 Uiso 1 1 calc R U . . .
C2 C 0.44865(17) 0.3079(2) 0.49018(16) 0.0322(6) Uani 1 1 d . . . . .
H2A H 0.4427 0.3094 0.5522 0.042 Uiso 1 1 calc R U . . .
H2B H 0.4952 0.3678 0.4901 0.042 Uiso 1 1 calc R U . . .
C3 C 0.48180(16) 0.1832(2) 0.47262(16) 0.0271(5) Uani 1 1 d . . . . .
H3 H 0.4381 0.1232 0.4811 0.035 Uiso 1 1 calc R U . . .
C4 C 0.47909(16) 0.1739(2) 0.37112(15) 0.0286(6) Uani 1 1 d . . . . .
H4A H 0.5251 0.2287 0.3624 0.037 Uiso 1 1 calc R U . . .
H4B H 0.4956 0.0926 0.3592 0.037 Uiso 1 1 calc R U . . .
C5 C 0.38190(17) 0.2048(2) 0.30096(17) 0.0353(6) Uani 1 1 d . . . . .
H5A H 0.3809 0.1981 0.2364 0.046 Uiso 1 1 calc R U . . .
H5B H 0.3357 0.1492 0.3083 0.046 Uiso 1 1 calc R U . . .
C6 C 0.35423(15) 0.4199(2) 0.26046(16) 0.0289(6) Uani 1 1 d . . . . .
C7 C 0.57884(17) 0.1581(2) 0.54524(17) 0.0307(6) Uani 1 1 d . . . . .
C8 C 0.8689(2) 0.4524(3) 0.6166(3) 0.0650(10) Uani 1 1 d . . . . .
H8A H 0.9324 0.4579 0.6612 0.084 Uiso 1 1 calc R U . . .
H8B H 0.8358 0.5257 0.6180 0.084 Uiso 1 1 calc R U . . .
H8C H 0.8696 0.4401 0.5538 0.084 Uiso 1 1 calc R U . . .
H1N2 H 0.634(2) 0.128(3) 0.676(2) 0.060(11) Uiso 1 1 d . . . . .
H2N1 H 0.536(2) 0.136(3) 0.6452(19) 0.041(9) Uiso 1 1 d . . . . .
H1O2 H 0.778(2) 0.378(3) 0.648(2) 0.069(12) Uiso 1 1 d . . . . .


_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 C6 1.710(2) . ?
S1 Na1 2.8700(14) 3_454 ?
S2 C6 1.715(3) . ?
S2 Na1 2.7845(12) 3_454 ?
Na1 O1 2.326(2) 2_656 ?
Na1 O1 2.3514(19) . ?
Na1 O2 2.368(3) . ?
Na1 S2 2.7845(12) 3_545 ?
Na1 S1 2.8700(14) 3_545 ?
Na1 C4 3.095(3) 2_656 ?
Na1 Na1 3.222(2) 2_656 ?
O1 C7 1.228(3) . ?
O1 Na1 2.326(2) 2_656 ?
N1 C6 1.333(3) . ?
N1 C5 1.461(3) . ?
N1 C1 1.463(3) . ?
O2 C8 1.385(4) . ?
O2 H1O2 0.79(3) . ?
N2 C7 1.324(3) . ?
N2 H1N2 0.82(3) . ?
N2 H2N1 0.79(3) . ?
C1 C2 1.520(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.527(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C7 1.513(3) . ?
C3 C4 1.518(3) . ?
C3 H3 0.9800 . ?
C4 C5 1.515(3) . ?
C4 Na1 3.095(3) 2_656 ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 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
C6 S1 Na1 87.15(9) . 3_454 ?
C6 S2 Na1 89.85(9) . 3_454 ?
O1 Na1 O1 92.50(7) 2_656 . ?
O1 Na1 O2 94.60(9) 2_656 . ?
O1 Na1 O2 91.89(9) . . ?
O1 Na1 S2 153.15(6) 2_656 3_545 ?
O1 Na1 S2 109.83(6) . 3_545 ?
O2 Na1 S2 99.22(7) . 3_545 ?
O1 Na1 S1 96.76(6) 2_656 3_545 ?
O1 Na1 S1 107.59(6) . 3_545 ?
O2 Na1 S1 156.91(7) . 3_545 ?
S2 Na1 S1 62.98(3) 3_545 3_545 ?
O1 Na1 C4 60.17(6) 2_656 2_656 ?
O1 Na1 C4 151.57(7) . 2_656 ?
O2 Na1 C4 83.36(8) . 2_656 ?
S2 Na1 C4 98.60(5) 3_545 2_656 ?
S1 Na1 C4 84.96(6) 3_545 2_656 ?
O1 Na1 Na1 46.79(5) 2_656 2_656 ?
O1 Na1 Na1 46.14(5) . 2_656 ?
O2 Na1 Na1 99.70(6) . 2_656 ?
S2 Na1 Na1 149.68(5) 3_545 2_656 ?
S1 Na1 Na1 102.74(2) 3_545 2_656 ?
C4 Na1 Na1 106.94(6) 2_656 2_656 ?
C7 O1 Na1 137.41(15) . 2_656 ?
C7 O1 Na1 135.04(16) . . ?
Na1 O1 Na1 87.08(7) 2_656 . ?
C6 N1 C5 123.3(2) . . ?
C6 N1 C1 124.9(2) . . ?
C5 N1 C1 111.3(2) . . ?
C8 O2 Na1 135.8(2) . . ?
C8 O2 H1O2 111(3) . . ?
Na1 O2 H1O2 108(3) . . ?
C7 N2 H1N2 119(2) . . ?
C7 N2 H2N1 121(2) . . ?
H1N2 N2 H2N1 120(3) . . ?
N1 C1 C2 110.70(19) . . ?
N1 C1 H1A 109.5 . . ?
C2 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 108.1 . . ?
C1 C2 C3 111.0(2) . . ?
C1 C2 H2A 109.4 . . ?
C3 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
C3 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C7 C3 C4 112.45(19) . . ?
C7 C3 C2 109.8(2) . . ?
C4 C3 C2 110.15(19) . . ?
C7 C3 H3 108.1 . . ?
C4 C3 H3 108.1 . . ?
C2 C3 H3 108.1 . . ?
C5 C4 C3 110.72(19) . . ?
C5 C4 Na1 142.35(16) . 2_656 ?
C3 C4 Na1 105.46(13) . 2_656 ?
C5 C4 H4A 109.5 . . ?
C3 C4 H4A 109.5 . . ?
Na1 C4 H4A 46.3 2_656 . ?
C5 C4 H4B 109.5 . . ?
C3 C4 H4B 109.5 . . ?
Na1 C4 H4B 66.2 2_656 . ?
H4A C4 H4B 108.1 . . ?
N1 C5 C4 108.7(2) . . ?
N1 C5 H5A 110.0 . . ?
C4 C5 H5A 110.0 . . ?
N1 C5 H5B 110.0 . . ?
C4 C5 H5B 110.0 . . ?
H5A C5 H5B 108.3 . . ?
N1 C6 S1 120.84(19) . . ?
N1 C6 S2 119.93(18) . . ?
S1 C6 S2 119.23(15) . . ?
O1 C7 N2 121.6(2) . . ?
O1 C7 C3 122.5(2) . . ?
N2 C7 C3 115.9(2) . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 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 C1 C2 -111.8(3) . . . . ?
C5 N1 C1 C2 60.6(3) . . . . ?
N1 C1 C2 C3 -54.3(3) . . . . ?
C1 C2 C3 C7 176.0(2) . . . . ?
C1 C2 C3 C4 51.6(3) . . . . ?
C7 C3 C4 C5 -177.6(2) . . . . ?
C2 C3 C4 C5 -54.8(3) . . . . ?
C7 C3 C4 Na1 -8.2(2) . . . 2_656 ?
C2 C3 C4 Na1 114.53(17) . . . 2_656 ?
C6 N1 C5 C4 109.6(2) . . . . ?
C1 N1 C5 C4 -62.9(3) . . . . ?
C3 C4 C5 N1 60.0(3) . . . . ?
Na1 C4 C5 N1 -103.1(3) 2_656 . . . ?
C5 N1 C6 S1 9.2(3) . . . . ?
C1 N1 C6 S1 -179.29(17) . . . . ?
C5 N1 C6 S2 -170.62(17) . . . . ?
C1 N1 C6 S2 0.9(3) . . . . ?
Na1 S1 C6 N1 171.62(19) 3_454 . . . ?
Na1 S1 C6 S2 -8.55(13) 3_454 . . . ?
Na1 S2 C6 N1 -171.36(19) 3_454 . . . ?
Na1 S2 C6 S1 8.81(13) 3_454 . . . ?
Na1 O1 C7 N2 162.0(2) 2_656 . . . ?
Na1 O1 C7 N2 -7.3(4) . . . . ?
Na1 O1 C7 C3 -18.3(4) 2_656 . . . ?
Na1 O1 C7 C3 172.40(18) . . . . ?
C4 C3 C7 O1 16.0(4) . . . . ?
C2 C3 C7 O1 -107.0(3) . . . . ?
C4 C3 C7 N2 -164.3(2) . . . . ?
C2 C3 C7 N2 72.7(3) . . . . ?

_refine_diff_density_max         0.378
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.060

####################################################################### 
# 
# 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_ap228
_database_code_depnum_ccdc_archive 'CCDC 1835871'
_audit_update_record             
;
2018-04-09 deposited with the CCDC.
2018-06-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H14 Au Br2 N O2 S2'
_chemical_formula_weight         589.12

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'
S S 0.1246 0.1234 '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'
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/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                   8.0665(4)
_cell_length_b                   16.5901(11)
_cell_length_c                   11.7403(6)
_cell_angle_alpha                90
_cell_angle_beta                 102.529(5)
_cell_angle_gamma                90
_cell_volume                     1533.72(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    298.0(1)
_cell_measurement_reflns_used    1448
_cell_measurement_theta_min      3.9170
_cell_measurement_theta_max      26.6190

_exptl_crystal_description       Parallelepiped
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.551
_exptl_crystal_F_000             1088
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    15.064
_shelx_estimated_absorpt_T_min   0.050
_shelx_estimated_absorpt_T_max   0.153
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.30787
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
crysalispro, agilent technologies, 
version 1.171.37.35 (release 13-08-2014 crysalis171 .net) 
(compiled aug 13 2014,18:06:01) 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298.0(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'enhance (mo) x-ray source'
_diffrn_measurement_device_type  'xcalibur, sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1048
_diffrn_reflns_number            6113
_diffrn_reflns_av_unetI/netI     0.0545
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.555
_diffrn_reflns_theta_max         25.350
_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             2814
_reflns_number_gt                2111
_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       
; 
crysalispro, agilent technologies, 
version 1.171.37.35 (release 13-08-2014 crysalis171 .net) 
(compiled aug 13 2014,18:06:01) 
;
_computing_cell_refinement       
; 
crysalispro, agilent technologies, 
version 1.171.37.35 (release 13-08-2014 crysalis171 .net) 
(compiled aug 13 2014,18:06:01) 
;
_computing_data_reduction        
; 
crysalispro, agilent technologies, 
version 1.171.37.35 (release 13-08-2014 crysalis171 .net) 
(compiled aug 13 2014,18:06:01) 
;
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    
'ORTEX - P. McArdle, J.Appl.Cryst.,1995,28,65-65.'
_computing_publication_material  
'Oscail - P. McArdle, J.Appl.Cryst.,2017,50,320-326.'
_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)+(0.0247P)²+0.8690P] 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         2814
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.0777
_refine_ls_wR_factor_gt          0.0669
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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 0.05002(4) 0.43545(2) 0.66125(3) 0.04430(13) Uani 1 1 d . . . . .
Br2 Br -0.24316(10) 0.41792(7) 0.67910(9) 0.0621(3) Uani 1 1 d . . . . .
Br1 Br 0.11027(12) 0.29193(7) 0.65804(9) 0.0696(3) Uani 1 1 d . . . . .
S2 S 0.0319(2) 0.57339(15) 0.6606(2) 0.0535(6) Uani 1 1 d . . . . .
S1 S 0.3162(2) 0.47903(16) 0.6459(2) 0.0534(6) Uani 1 1 d . . . . .
N1 N 0.3248(7) 0.6416(5) 0.6404(5) 0.0460(19) Uani 1 1 d . . . . .
O2 O 0.6563(10) 0.8928(6) 0.5538(6) 0.105(3) Uani 1 1 d . . . . .
O1 O 0.4665(8) 0.8544(5) 0.4017(6) 0.092(3) Uani 1 1 d . . . . .
C1 C 0.2415(9) 0.5760(5) 0.6478(6) 0.040(2) Uani 1 1 d . . . . .
C2 C 0.2505(10) 0.7211(6) 0.6533(8) 0.055(2) Uani 1 1 d . . . . .
H2A H 0.289985 0.739958 0.732761 0.072 Uiso 1 1 calc R U . . .
H2B H 0.127822 0.716410 0.638338 0.072 Uiso 1 1 calc R U . . .
C3 C 0.2984(10) 0.7814(6) 0.5703(7) 0.059(3) Uani 1 1 d . . . . .
H3A H 0.246347 0.766092 0.490873 0.076 Uiso 1 1 calc R U . . .
H3B H 0.255073 0.834021 0.584982 0.076 Uiso 1 1 calc R U . . .
C4 C 0.4875(10) 0.7863(6) 0.5833(7) 0.052(3) Uani 1 1 d . . . . .
H4 H 0.539626 0.802219 0.663482 0.068 Uiso 1 1 calc R U . . .
C5 C 0.5535(10) 0.7040(6) 0.5593(8) 0.061(3) Uani 1 1 d . . . . .
H5A H 0.675941 0.706649 0.569371 0.080 Uiso 1 1 calc R U . . .
H5B H 0.506073 0.689411 0.478786 0.080 Uiso 1 1 calc R U . . .
C6 C 0.5087(9) 0.6387(6) 0.6395(7) 0.053(2) Uani 1 1 d . . . . .
H6A H 0.536646 0.586152 0.612752 0.069 Uiso 1 1 calc R U . . .
H6B H 0.575027 0.646632 0.718103 0.069 Uiso 1 1 calc R U . . .
C7 C 0.5332(12) 0.8470(6) 0.5003(9) 0.059(3) Uani 1 1 d . . . . .
C8 C 0.7178(13) 0.9635(8) 0.4851(10) 0.096(4) Uani 1 1 d . . . . .
H8A H 0.629740 0.981893 0.420376 0.124 Uiso 1 1 calc R U . . .
H8B H 0.761635 1.008567 0.535206 0.124 Uiso 1 1 calc R U . . .
C9 C 0.8509(16) 0.9195(8) 0.4466(12) 0.120(5) Uani 1 1 d . . . . .
H9A H 0.932612 0.900649 0.513260 0.157 Uiso 1 1 calc R U . . .
H9B H 0.905810 0.954396 0.400920 0.157 Uiso 1 1 calc R U . . .
H9C H 0.802419 0.874292 0.399952 0.157 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 S2 2.293(3) . ?
Au1 S1 2.309(2) . ?
Au1 Br1 2.4322(12) . ?
Au1 Br2 2.4365(8) . ?
S2 C1 1.730(7) . ?
S1 C1 1.720(9) . ?
N1 C1 1.292(10) . ?
N1 C2 1.469(10) . ?
N1 C6 1.486(9) . ?
O2 C7 1.299(11) . ?
O2 C8 1.564(13) . ?
O1 C7 1.172(10) . ?
C2 C3 1.504(11) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.501(10) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C7 1.503(12) . ?
C4 C5 1.514(12) . ?
C4 H4 0.9800 . ?
C5 C6 1.530(11) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C8 C9 1.449(14) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 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
S2 Au1 S1 75.35(8) . . ?
S2 Au1 Br1 171.82(5) . . ?
S1 Au1 Br1 96.49(7) . . ?
S2 Au1 Br2 93.27(5) . . ?
S1 Au1 Br2 168.61(7) . . ?
Br1 Au1 Br2 94.90(4) . . ?
C1 S2 Au1 87.9(3) . . ?
C1 S1 Au1 87.6(3) . . ?
C1 N1 C2 121.3(7) . . ?
C1 N1 C6 120.5(8) . . ?
C2 N1 C6 117.4(7) . . ?
C7 O2 C8 118.9(8) . . ?
N1 C1 S1 126.8(6) . . ?
N1 C1 S2 124.0(7) . . ?
S1 C1 S2 109.2(5) . . ?
N1 C2 C3 111.2(7) . . ?
N1 C2 H2A 109.4 . . ?
C3 C2 H2A 109.4 . . ?
N1 C2 H2B 109.4 . . ?
C3 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C4 C3 C2 111.6(7) . . ?
C4 C3 H3A 109.3 . . ?
C2 C3 H3A 109.3 . . ?
C4 C3 H3B 109.3 . . ?
C2 C3 H3B 109.3 . . ?
H3A C3 H3B 108.0 . . ?
C3 C4 C7 110.9(7) . . ?
C3 C4 C5 108.8(7) . . ?
C7 C4 C5 109.7(8) . . ?
C3 C4 H4 109.1 . . ?
C7 C4 H4 109.1 . . ?
C5 C4 H4 109.1 . . ?
C4 C5 C6 112.6(7) . . ?
C4 C5 H5A 109.1 . . ?
C6 C5 H5A 109.1 . . ?
C4 C5 H5B 109.1 . . ?
C6 C5 H5B 109.1 . . ?
H5A C5 H5B 107.8 . . ?
N1 C6 C5 110.5(7) . . ?
N1 C6 H6A 109.5 . . ?
C5 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
O1 C7 O2 123.7(10) . . ?
O1 C7 C4 125.9(9) . . ?
O2 C7 C4 110.3(9) . . ?
C9 C8 O2 97.1(11) . . ?
C9 C8 H8A 112.3 . . ?
O2 C8 H8A 112.3 . . ?
C9 C8 H8B 112.3 . . ?
O2 C8 H8B 112.3 . . ?
H8A C8 H8B 109.9 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 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 S1 -174.6(6) . . . . ?
C6 N1 C1 S1 -5.4(11) . . . . ?
C2 N1 C1 S2 5.7(11) . . . . ?
C6 N1 C1 S2 174.9(6) . . . . ?
Au1 S1 C1 N1 -179.1(7) . . . . ?
Au1 S1 C1 S2 0.6(4) . . . . ?
Au1 S2 C1 N1 179.1(7) . . . . ?
Au1 S2 C1 S1 -0.6(4) . . . . ?
C1 N1 C2 C3 -141.8(7) . . . . ?
C6 N1 C2 C3 48.7(10) . . . . ?
N1 C2 C3 C4 -54.6(10) . . . . ?
C2 C3 C4 C7 -179.7(8) . . . . ?
C2 C3 C4 C5 59.5(10) . . . . ?
C3 C4 C5 C6 -57.5(9) . . . . ?
C7 C4 C5 C6 -179.0(7) . . . . ?
C1 N1 C6 C5 144.3(8) . . . . ?
C2 N1 C6 C5 -46.0(10) . . . . ?
C4 C5 C6 N1 49.9(10) . . . . ?
C8 O2 C7 O1 1.6(17) . . . . ?
C8 O2 C7 C4 -176.7(9) . . . . ?
C3 C4 C7 O1 -44.1(15) . . . . ?
C5 C4 C7 O1 76.2(13) . . . . ?
C3 C4 C7 O2 134.1(9) . . . . ?
C5 C4 C7 O2 -105.6(10) . . . . ?
C7 O2 C8 C9 -92.4(12) . . . . ?

_refine_diff_density_max         0.816
_refine_diff_density_min         -0.908
_refine_diff_density_rms         0.169

####################################################################### 
# 
# 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_ap226
_database_code_depnum_ccdc_archive 'CCDC 1835870'
_audit_update_record             
;
2018-04-09 deposited with the CCDC.
2018-06-14 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT910_ap226               
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         11 Note
RESPONSE: These reflections are behind the beam stop.
;
# Added during the CSD deposition process: Monday 09 April 2018 04:10 PM
# end Validation Reply Form


_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            'C18 H28 N2 O4 S4 Zn'
_chemical_formula_weight         530.03

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'
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'
Zn Zn 0.2839 1.4301 '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                   9.4775(7)
_cell_length_b                   10.8781(8)
_cell_length_c                   12.1158(9)
_cell_angle_alpha                81.181(6)
_cell_angle_beta                 72.125(6)
_cell_angle_gamma                81.757(6)
_cell_volume                     1168.58(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    299.0(2)
_cell_measurement_reflns_used    1985
_cell_measurement_theta_min      3.7470
_cell_measurement_theta_max      26.9460

_exptl_crystal_description       Parallelepiped
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_F_000             552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    1.435
_shelx_estimated_absorpt_T_min   0.534
_shelx_estimated_absorpt_T_max   0.762
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.87706
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
crysalispro, agilent technologies, 
version 1.171.37.35 (release 13-08-2014 crysalis171 .net) 
(compiled aug 13 2014,18:06:01) 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      299.0(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'enhance (mo) x-ray source'
_diffrn_measurement_device_type  'xcalibur, sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1048
_diffrn_reflns_number            9243
_diffrn_reflns_av_unetI/netI     0.0861
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.558
_diffrn_reflns_theta_max         29.223
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.842
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.842
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.842
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5332
_reflns_number_gt                3170
_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       
; 
crysalispro, agilent technologies, 
version 1.171.37.35 (release 13-08-2014 crysalis171 .net) 
(compiled aug 13 2014,18:06:01) 
;
_computing_cell_refinement       
; 
crysalispro, agilent technologies, 
version 1.171.37.35 (release 13-08-2014 crysalis171 .net) 
(compiled aug 13 2014,18:06:01) 
;
_computing_data_reduction        
; 
crysalispro, agilent technologies, 
version 1.171.37.35 (release 13-08-2014 crysalis171 .net) 
(compiled aug 13 2014,18:06:01) 
;
_computing_structure_solution    
'SHELXT - G.M.Sheldrick,Acta Crystallogr.A71(2015)3-8.'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'ORTEX - P. McArdle, J.Appl.Cryst.,1995,28,65-65.'
_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)+(0.0574P)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_number_reflns         5332
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0950
_refine_ls_R_factor_gt           0.0470
_refine_ls_wR_factor_ref         0.1211
_refine_ls_wR_factor_gt          0.0984
_refine_ls_goodness_of_fit_ref   0.857
_refine_ls_restrained_S_all      0.857
_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
Zn1 Zn 0.45123(5) 0.84044(4) 0.49752(4) 0.04328(16) Uani 1 1 d . . . . .
S3 S 0.68763(11) 0.99024(9) 0.40166(8) 0.0399(2) Uani 1 1 d . . . . .
S4 S 0.47494(12) 0.90803(10) 0.30096(8) 0.0475(3) Uani 1 1 d . . . . .
S2 S 0.58124(11) 0.68674(10) 0.59657(9) 0.0454(3) Uani 1 1 d . . . . .
S1 S 0.29728(12) 0.66633(10) 0.55386(9) 0.0457(3) Uani 1 1 d . . . . .
O2 O 0.2064(3) 0.2775(3) 1.1103(2) 0.0582(8) Uani 1 1 d . . . . .
N1 N 0.4212(3) 0.4938(3) 0.6859(2) 0.0389(7) Uani 1 1 d . . . . .
O4 O 0.8448(3) 1.2185(3) -0.2358(2) 0.0740(10) Uani 1 1 d . . . . .
N2 N 0.6448(4) 1.0888(3) 0.1965(3) 0.0480(8) Uani 1 1 d . . . . .
O3 O 1.0407(4) 1.1609(4) -0.1674(3) 0.0824(11) Uani 1 1 d . . . . .
O1 O 0.2001(5) 0.4837(3) 1.0855(3) 0.1047(14) Uani 1 1 d . . . . .
C1 C 0.4325(4) 0.6030(3) 0.6193(3) 0.0370(8) Uani 1 1 d . . . . .
C2 C 0.2906(5) 0.4254(4) 0.7167(3) 0.0507(10) Uani 1 1 d . . . . .
H2A H 0.3210 0.3397 0.6994 0.066 Uiso 1 1 calc R U . . .
H2B H 0.2246 0.4637 0.6709 0.066 Uiso 1 1 calc R U . . .
C3 C 0.2092(4) 0.4269(4) 0.8460(3) 0.0507(11) Uani 1 1 d . . . . .
H3A H 0.1249 0.3780 0.8671 0.066 Uiso 1 1 calc R U . . .
H3B H 0.1717 0.5121 0.8619 0.066 Uiso 1 1 calc R U . . .
C4 C 0.3145(5) 0.3725(4) 0.9195(3) 0.0494(10) Uani 1 1 d . . . . .
H4 H 0.3414 0.2834 0.9105 0.064 Uiso 1 1 calc R U . . .
C5 C 0.4546(4) 0.4374(4) 0.8794(3) 0.0445(9) Uani 1 1 d . . . . .
H5A H 0.5238 0.3953 0.9211 0.058 Uiso 1 1 calc R U . . .
H5B H 0.4305 0.5228 0.8986 0.058 Uiso 1 1 calc R U . . .
C6 C 0.5291(4) 0.4388(4) 0.7489(3) 0.0451(10) Uani 1 1 d . . . . .
H6A H 0.6138 0.4875 0.7254 0.059 Uiso 1 1 calc R U . . .
H6B H 0.5649 0.3542 0.7302 0.059 Uiso 1 1 calc R U . . .
C7 C 0.2338(5) 0.3858(4) 1.0471(4) 0.0557(11) Uani 1 1 d . . . . .
C8 C 0.1265(6) 0.2825(5) 1.2336(4) 0.0771(16) Uani 1 1 d . . . . .
H8A H 0.0273 0.3253 1.2425 0.100 Uiso 1 1 calc R U . . .
H8B H 0.1792 0.3271 1.2695 0.100 Uiso 1 1 calc R U . . .
C9 C 0.1177(6) 0.1509(6) 1.2897(4) 0.098(2) Uani 1 1 d . . . . .
H9A H 0.0809 0.1041 1.2453 0.127 Uiso 1 1 calc R U . . .
H9B H 0.0515 0.1498 1.3677 0.127 Uiso 1 1 calc R U . . .
H9C H 0.2152 0.1140 1.2923 0.127 Uiso 1 1 calc R U . . .
C10 C 0.6071(4) 1.0041(3) 0.2889(3) 0.0396(9) Uani 1 1 d . . . . .
C11 C 0.7551(5) 1.1773(4) 0.1792(3) 0.0525(11) Uani 1 1 d . . . . .
H11A H 0.8030 1.1580 0.2409 0.068 Uiso 1 1 calc R U . . .
H11B H 0.7052 1.2615 0.1836 0.068 Uiso 1 1 calc R U . . .
C12 C 0.8698(5) 1.1712(4) 0.0643(3) 0.0524(11) Uani 1 1 d . . . . .
H12A H 0.9259 1.0893 0.0625 0.068 Uiso 1 1 calc R U . . .
H12B H 0.9386 1.2330 0.0535 0.068 Uiso 1 1 calc R U . . .
C13 C 0.7979(4) 1.1955(4) -0.0351(3) 0.0463(10) Uani 1 1 d . . . . .
H13 H 0.7466 1.2804 -0.0337 0.060 Uiso 1 1 calc R U . . .
C14 C 0.6807(5) 1.1055(4) -0.0125(3) 0.0590(12) Uani 1 1 d . . . . .
H14A H 0.6299 1.1250 -0.0724 0.077 Uiso 1 1 calc R U . . .
H14B H 0.7290 1.0208 -0.0173 0.077 Uiso 1 1 calc R U . . .
C15 C 0.5701(5) 1.1129(5) 0.1035(3) 0.0613(12) Uani 1 1 d . . . . .
H15A H 0.5151 1.1953 0.1060 0.080 Uiso 1 1 calc R U . . .
H15B H 0.4998 1.0518 0.1166 0.080 Uiso 1 1 calc R U . . .
C16 C 0.9105(5) 1.1895(4) -0.1515(3) 0.0505(10) Uani 1 1 d . . . . .
C17 C 0.9388(6) 1.2180(6) -0.3552(4) 0.0904(19) Uani 1 1 d . . . . .
H17A H 0.8854 1.1918 -0.4027 0.117 Uiso 1 1 calc R U . . .
H17B H 1.0271 1.1597 -0.3581 0.117 Uiso 1 1 calc R U . . .
C18 C 0.9822(6) 1.3453(7) -0.4009(5) 0.116(3) Uani 1 1 d . . . . .
H18A H 0.8972 1.3991 -0.4127 0.151 Uiso 1 1 calc R U . . .
H18B H 1.0594 1.3426 -0.4738 0.151 Uiso 1 1 calc R U . . .
H18C H 1.0182 1.3768 -0.3458 0.151 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
Zn1 S4 2.3334(11) . ?
Zn1 S2 2.3357(11) . ?
Zn1 S3 2.3716(10) 2_676 ?
Zn1 S1 2.4426(11) . ?
Zn1 S3 2.8095(11) . ?
S3 C10 1.737(4) . ?
S3 Zn1 2.3716(10) 2_676 ?
S4 C10 1.703(4) . ?
S2 C1 1.716(4) . ?
S1 C1 1.717(4) . ?
O2 C7 1.316(5) . ?
O2 C8 1.458(5) . ?
N1 C1 1.328(5) . ?
N1 C2 1.456(5) . ?
N1 C6 1.466(4) . ?
O4 C16 1.330(5) . ?
O4 C17 1.448(5) . ?
N2 C10 1.327(5) . ?
N2 C11 1.469(5) . ?
N2 C15 1.477(5) . ?
O3 C16 1.191(5) . ?
O1 C7 1.189(5) . ?
C2 C3 1.520(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.534(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.505(5) . ?
C4 C7 1.519(5) . ?
C4 H4 0.9800 . ?
C5 C6 1.520(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C8 C9 1.490(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C11 C12 1.484(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.529(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C16 1.489(5) . ?
C13 C14 1.521(5) . ?
C13 H13 0.9800 . ?
C14 C15 1.479(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C17 C18 1.476(8) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
S4 Zn1 S2 134.30(4) . . ?
S4 Zn1 S3 104.85(4) . 2_676 ?
S2 Zn1 S3 117.89(4) . 2_676 ?
S4 Zn1 S1 107.13(4) . . ?
S2 Zn1 S1 75.79(4) . . ?
S3 Zn1 S1 107.56(4) 2_676 . ?
S4 Zn1 S3 69.34(3) . . ?
S2 Zn1 S3 95.45(4) . . ?
S3 Zn1 S3 88.24(3) 2_676 . ?
S1 Zn1 S3 164.10(4) . . ?
C10 S3 Zn1 99.89(12) . 2_676 ?
C10 S3 Zn1 77.67(13) . . ?
Zn1 S3 Zn1 91.76(3) 2_676 . ?
C10 S4 Zn1 93.47(13) . . ?
C1 S2 Zn1 84.84(13) . . ?
C1 S1 Zn1 81.55(13) . . ?
C7 O2 C8 116.0(4) . . ?
C1 N1 C2 123.3(3) . . ?
C1 N1 C6 123.2(3) . . ?
C2 N1 C6 113.0(3) . . ?
C16 O4 C17 117.5(4) . . ?
C10 N2 C11 124.5(3) . . ?
C10 N2 C15 123.6(3) . . ?
C11 N2 C15 111.7(3) . . ?
N1 C1 S2 121.4(3) . . ?
N1 C1 S1 121.0(3) . . ?
S2 C1 S1 117.6(2) . . ?
N1 C2 C3 109.7(3) . . ?
N1 C2 H2A 109.7 . . ?
C3 C2 H2A 109.7 . . ?
N1 C2 H2B 109.7 . . ?
C3 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
C2 C3 C4 110.4(3) . . ?
C2 C3 H3A 109.6 . . ?
C4 C3 H3A 109.6 . . ?
C2 C3 H3B 109.6 . . ?
C4 C3 H3B 109.6 . . ?
H3A C3 H3B 108.1 . . ?
C5 C4 C7 110.8(3) . . ?
C5 C4 C3 110.7(3) . . ?
C7 C4 C3 109.0(3) . . ?
C5 C4 H4 108.8 . . ?
C7 C4 H4 108.8 . . ?
C3 C4 H4 108.8 . . ?
C4 C5 C6 112.3(3) . . ?
C4 C5 H5A 109.1 . . ?
C6 C5 H5A 109.1 . . ?
C4 C5 H5B 109.1 . . ?
C6 C5 H5B 109.1 . . ?
H5A C5 H5B 107.9 . . ?
N1 C6 C5 109.3(3) . . ?
N1 C6 H6A 109.8 . . ?
C5 C6 H6A 109.8 . . ?
N1 C6 H6B 109.8 . . ?
C5 C6 H6B 109.8 . . ?
H6A C6 H6B 108.3 . . ?
O1 C7 O2 123.9(4) . . ?
O1 C7 C4 123.5(4) . . ?
O2 C7 C4 112.7(4) . . ?
O2 C8 C9 107.1(4) . . ?
O2 C8 H8A 110.3 . . ?
C9 C8 H8A 110.3 . . ?
O2 C8 H8B 110.3 . . ?
C9 C8 H8B 110.3 . . ?
H8A C8 H8B 108.6 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N2 C10 S4 120.5(3) . . ?
N2 C10 S3 121.3(3) . . ?
S4 C10 S3 118.2(2) . . ?
N2 C11 C12 111.1(3) . . ?
N2 C11 H11A 109.4 . . ?
C12 C11 H11A 109.4 . . ?
N2 C11 H11B 109.4 . . ?
C12 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C11 C12 C13 111.0(3) . . ?
C11 C12 H12A 109.4 . . ?
C13 C12 H12A 109.4 . . ?
C11 C12 H12B 109.4 . . ?
C13 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C16 C13 C14 112.5(3) . . ?
C16 C13 C12 112.1(3) . . ?
C14 C13 C12 109.3(3) . . ?
C16 C13 H13 107.6 . . ?
C14 C13 H13 107.6 . . ?
C12 C13 H13 107.6 . . ?
C15 C14 C13 111.6(3) . . ?
C15 C14 H14A 109.3 . . ?
C13 C14 H14A 109.3 . . ?
C15 C14 H14B 109.3 . . ?
C13 C14 H14B 109.3 . . ?
H14A C14 H14B 108.0 . . ?
N2 C15 C14 110.6(3) . . ?
N2 C15 H15A 109.5 . . ?
C14 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
O3 C16 O4 124.5(4) . . ?
O3 C16 C13 125.2(4) . . ?
O4 C16 C13 110.3(4) . . ?
O4 C17 C18 109.0(5) . . ?
O4 C17 H17A 109.9 . . ?
C18 C17 H17A 109.9 . . ?
O4 C17 H17B 109.9 . . ?
C18 C17 H17B 109.9 . . ?
H17A C17 H17B 108.3 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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 S2 173.9(3) . . . . ?
C6 N1 C1 S2 2.7(5) . . . . ?
C2 N1 C1 S1 -5.3(5) . . . . ?
C6 N1 C1 S1 -176.6(2) . . . . ?
Zn1 S2 C1 N1 -174.5(3) . . . . ?
Zn1 S2 C1 S1 4.82(17) . . . . ?
Zn1 S1 C1 N1 174.6(3) . . . . ?
Zn1 S1 C1 S2 -4.64(17) . . . . ?
C1 N1 C2 C3 -110.7(4) . . . . ?
C6 N1 C2 C3 61.3(4) . . . . ?
N1 C2 C3 C4 -56.6(4) . . . . ?
C2 C3 C4 C5 52.9(4) . . . . ?
C2 C3 C4 C7 175.1(3) . . . . ?
C7 C4 C5 C6 -173.5(3) . . . . ?
C3 C4 C5 C6 -52.4(4) . . . . ?
C1 N1 C6 C5 112.5(4) . . . . ?
C2 N1 C6 C5 -59.5(4) . . . . ?
C4 C5 C6 N1 54.6(4) . . . . ?
C8 O2 C7 O1 1.6(7) . . . . ?
C8 O2 C7 C4 -178.9(3) . . . . ?
C5 C4 C7 O1 53.4(6) . . . . ?
C3 C4 C7 O1 -68.7(6) . . . . ?
C5 C4 C7 O2 -126.1(4) . . . . ?
C3 C4 C7 O2 111.8(4) . . . . ?
C7 O2 C8 C9 -175.9(4) . . . . ?
C11 N2 C10 S4 178.8(3) . . . . ?
C15 N2 C10 S4 4.6(5) . . . . ?
C11 N2 C10 S3 0.1(5) . . . . ?
C15 N2 C10 S3 -174.0(3) . . . . ?
Zn1 S4 C10 N2 -166.9(3) . . . . ?
Zn1 S4 C10 S3 11.8(2) . . . . ?
Zn1 S3 C10 N2 79.1(3) 2_676 . . . ?
Zn1 S3 C10 N2 168.7(3) . . . . ?
Zn1 S3 C10 S4 -99.6(2) 2_676 . . . ?
Zn1 S3 C10 S4 -10.00(18) . . . . ?
C10 N2 C11 C12 127.1(4) . . . . ?
C15 N2 C11 C12 -58.2(5) . . . . ?
N2 C11 C12 C13 56.6(5) . . . . ?
C11 C12 C13 C16 -179.8(3) . . . . ?
C11 C12 C13 C14 -54.4(5) . . . . ?
C16 C13 C14 C15 179.9(4) . . . . ?
C12 C13 C14 C15 54.8(5) . . . . ?
C10 N2 C15 C14 -127.3(4) . . . . ?
C11 N2 C15 C14 57.9(5) . . . . ?
C13 C14 C15 N2 -56.6(5) . . . . ?
C17 O4 C16 O3 -1.6(7) . . . . ?
C17 O4 C16 C13 179.6(4) . . . . ?
C14 C13 C16 O3 -118.7(5) . . . . ?
C12 C13 C16 O3 4.9(6) . . . . ?
C14 C13 C16 O4 60.1(5) . . . . ?
C12 C13 C16 O4 -176.3(4) . . . . ?
C16 O4 C17 C18 -92.7(6) . . . . ?

_refine_diff_density_max         0.537
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.070

