# Electronic Supplementary Material (ESI) for Metallomics.
# 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_L3
_database_code_depnum_ccdc_archive 'CCDC 1857559'
_audit_update_record             
;
2018-07-23 deposited with the CCDC.
2018-11-12 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         'C15 H20 N4 O4 S2'
_chemical_formula_sum            'C15 H20 N4 O4 S2'
_chemical_formula_weight         384.47

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'
Hg Hg -2.3894 9.2266 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   7.2921(6)
_cell_length_b                   7.8235(6)
_cell_length_c                   30.636(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.610(3)
_cell_angle_gamma                90
_cell_volume                     1744.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4184
_cell_measurement_theta_min      3.82
_cell_measurement_theta_max      26.08

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_F_000             808.0
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.246
_exptl_crystal_size_mid          0.166
_exptl_crystal_size_min          0.098
_exptl_absorpt_coefficient_mu    0.334
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.936
_exptl_absorpt_correction_T_max  0.968
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   X-ray
_diffrn_measurement_device_type  'Bruker PHOTON100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13043
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         2.665
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1795
_reflns_number_gt                1460
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0290P)²+2.3089P] 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         1795
_refine_ls_number_parameters     115
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.0957
_refine_ls_wR_factor_gt          0.0878
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.093
_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
S1 S 0.75848(8) 0.67935(8) 0.68020(2) 0.04719(19) Uani 1 1 d . . . . .
N2 N 0.4049(2) 0.7501(2) 0.65143(5) 0.0357(4) Uani 1 1 d . . . . .
N1 N 0.4265(2) 0.6172(2) 0.71343(5) 0.0346(4) Uani 1 1 d . . . . .
O1 O 0.3969(3) 0.2498(2) 0.54892(6) 0.0589(5) Uani 1 1 d . . . . .
H1 H 0.3493 0.1915 0.5291 0.088 Uiso 1 1 calc R U . . .
O2 O 0.2590(3) 0.4586(2) 0.51053(6) 0.0647(5) Uani 1 1 d . . . . .
C2 C 0.5290(3) 0.6835(3) 0.68166(6) 0.0319(4) Uani 1 1 d . . . . .
C4 C 0.2285(3) 0.7222(3) 0.66411(7) 0.0415(5) Uani 1 1 d . . . . .
H4 H 0.1202 0.7549 0.6487 0.050 Uiso 1 1 calc R U . . .
C3 C 0.2412(3) 0.6405(3) 0.70211(7) 0.0393(5) Uani 1 1 d . . . . .
H3 H 0.1439 0.6054 0.7182 0.047 Uiso 1 1 calc R U . . .
C8 C 0.3571(3) 0.4102(3) 0.54189(7) 0.0411(5) Uani 1 1 d . . . . .
C5 C 0.4505(3) 0.8220(3) 0.60964(7) 0.0423(5) Uani 1 1 d . . . . .
H5A H 0.5830 0.8307 0.6089 0.051 Uiso 1 1 calc R U . . .
H5B H 0.3995 0.9362 0.6066 0.051 Uiso 1 1 calc R U . . .
C1 C 0.5000 0.5159(4) 0.7500 0.0381(7) Uani 1 2 d S T P . .
H1A H 0.5966 0.4427 0.7402 0.046 Uiso 0.5 1 calc R U P . .
H1B H 0.4034 0.4427 0.7598 0.046 Uiso 0.5 1 calc R U P . .
C6 C 0.3756(3) 0.7119(3) 0.57163(7) 0.0439(5) Uani 1 1 d . . . . .
H6A H 0.2424 0.7146 0.5704 0.053 Uiso 1 1 calc R U . . .
H6B H 0.4150 0.7592 0.5445 0.053 Uiso 1 1 calc R U . . .
C7 C 0.4401(3) 0.5276(3) 0.57590(7) 0.0433(5) Uani 1 1 d . . . . .
H7A H 0.5726 0.5251 0.5745 0.052 Uiso 1 1 calc R U . . .
H7B H 0.4117 0.4852 0.6045 0.052 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
S1 C2 1.677(2) . ?
N2 C2 1.358(3) . ?
N2 C4 1.384(3) . ?
N2 C5 1.456(3) . ?
N1 C2 1.366(3) . ?
N1 C3 1.385(3) . ?
N1 C1 1.448(2) . ?
O1 C8 1.303(3) . ?
O1 H1 0.8200 . ?
O2 C8 1.222(3) . ?
C4 C3 1.326(3) . ?
C4 H4 0.9300 . ?
C3 H3 0.9300 . ?
C8 C7 1.489(3) . ?
C5 C6 1.522(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C1 N1 1.448(2) 2_656 ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C6 C7 1.519(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?

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 N2 C4 109.82(18) . . ?
C2 N2 C5 124.68(18) . . ?
C4 N2 C5 125.14(18) . . ?
C2 N1 C3 109.93(17) . . ?
C2 N1 C1 124.50(15) . . ?
C3 N1 C1 124.98(15) . . ?
C8 O1 H1 109.5 . . ?
N2 C2 N1 105.10(17) . . ?
N2 C2 S1 127.77(16) . . ?
N1 C2 S1 127.13(16) . . ?
C3 C4 N2 107.93(19) . . ?
C3 C4 H4 126.0 . . ?
N2 C4 H4 126.0 . . ?
C4 C3 N1 107.21(19) . . ?
C4 C3 H3 126.4 . . ?
N1 C3 H3 126.4 . . ?
O2 C8 O1 122.8(2) . . ?
O2 C8 C7 123.4(2) . . ?
O1 C8 C7 113.72(19) . . ?
N2 C5 C6 111.32(18) . . ?
N2 C5 H5A 109.4 . . ?
C6 C5 H5A 109.4 . . ?
N2 C5 H5B 109.4 . . ?
C6 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
N1 C1 N1 113.6(2) . 2_656 ?
N1 C1 H1A 108.9 . . ?
N1 C1 H1A 108.9 2_656 . ?
N1 C1 H1B 108.9 . . ?
N1 C1 H1B 108.9 2_656 . ?
H1A C1 H1B 107.7 . . ?
C7 C6 C5 112.12(18) . . ?
C7 C6 H6A 109.2 . . ?
C5 C6 H6A 109.2 . . ?
C7 C6 H6B 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C8 C7 C6 114.53(19) . . ?
C8 C7 H7A 108.6 . . ?
C6 C7 H7A 108.6 . . ?
C8 C7 H7B 108.6 . . ?
C6 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?

_refine_diff_density_max         0.203
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.042



