# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1017715'
_audit_update_record             
;
2014-08-03 deposited with the CCDC.
2014-11-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H13 Cl2 Hg N3 O3 S'
_chemical_formula_sum            'C16 H13 Cl2 Hg N3 O3 S'
_chemical_formula_weight         598.84

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'
Cl Cl 0.1484 0.1585 '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'
Hg Hg -2.3894 9.2266 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.9121(5)
_cell_length_b                   7.7803(3)
_cell_length_c                   18.6223(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.4640(10)
_cell_angle_gamma                90.00
_cell_volume                     1865.12(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8992
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      26.30

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.133
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1136
_exptl_absorpt_coefficient_mu    8.672
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1503
_exptl_absorpt_correction_T_max  0.2294
_exptl_absorpt_process_details   'SADABS (N|Bruker, 2004)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            26561
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_sigmaI/netI    0.0302
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.19
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3661
_reflns_number_gt                2934
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'



_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0351P)²+9.6930P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3661
_refine_ls_number_parameters     239
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0336
_refine_ls_wR_factor_ref         0.0970
_refine_ls_wR_factor_gt          0.0899
_refine_ls_goodness_of_fit_ref   1.187
_refine_ls_restrained_S_all      1.187
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5523(6) -0.0841(11) 0.0998(4) 0.0383(19) Uani 1 1 d . . .
H1 H 0.5750 -0.1946 0.0903 0.046 Uiso 1 1 calc R . .
C2 C 0.5949(6) 0.0527(13) 0.0677(5) 0.048(2) Uani 1 1 d . . .
H2 H 0.6463 0.0354 0.0362 0.058 Uiso 1 1 calc R . .
C3 C 0.5625(7) 0.2148(13) 0.0814(5) 0.051(2) Uani 1 1 d . . .
H3 H 0.5914 0.3070 0.0583 0.062 Uiso 1 1 calc R . .
C4 C 0.4876(6) 0.2459(10) 0.1290(5) 0.0420(19) Uani 1 1 d . . .
H4 H 0.4681 0.3577 0.1393 0.050 Uiso 1 1 calc R . .
C5 C 0.4416(5) 0.1052(9) 0.1615(4) 0.0304(16) Uani 1 1 d . . .
C6 C 0.4742(5) -0.0597(9) 0.1473(4) 0.0312(16) Uani 1 1 d . . .
C7 C 0.4252(5) -0.2083(9) 0.1776(4) 0.0314(16) Uani 1 1 d . . .
C8 C 0.3401(5) -0.1773(9) 0.2272(4) 0.0266(15) Uani 1 1 d . . .
C9 C 0.3187(5) -0.0152(9) 0.2463(4) 0.0282(15) Uani 1 1 d . . .
C10 C 0.3644(5) 0.1357(10) 0.2133(4) 0.0338(17) Uani 1 1 d . . .
C11 C 0.1967(5) -0.3481(9) 0.2680(4) 0.0267(15) Uani 1 1 d . . .
C12 C 0.0395(5) -0.4304(9) 0.3189(4) 0.0308(16) Uani 1 1 d . . .
C13 C 0.0293(6) -0.3213(10) 0.2653(4) 0.0349(17) Uani 1 1 d . . .
H13 H -0.0354 -0.2782 0.2489 0.042 Uiso 1 1 calc R . .
C14 C 0.2396(9) -0.871(2) 0.5113(7) 0.094(4) Uani 1 1 d . . .
H14A H 0.2873 -0.9193 0.5480 0.141 Uiso 1 1 calc R . .
H14B H 0.2620 -0.7575 0.4996 0.141 Uiso 1 1 calc R . .
H14C H 0.2375 -0.9420 0.4691 0.141 Uiso 1 1 calc R . .
C15 C 0.1300(10) -0.9210(13) 0.6090(6) 0.069(3) Uani 1 1 d . . .
H15A H 0.1966 -0.9605 0.6290 0.103 Uiso 1 1 calc R . .
H15B H 0.0809 -1.0136 0.6086 0.103 Uiso 1 1 calc R . .
H15C H 0.1068 -0.8282 0.6377 0.103 Uiso 1 1 calc R . .
C16 C 0.0597(8) -0.8014(12) 0.4962(6) 0.058(3) Uani 1 1 d . . .
H16 H -0.0037 -0.7910 0.5164 0.070 Uiso 1 1 calc R . .
N1 N 0.2981(5) -0.3254(8) 0.2499(3) 0.0314(14) Uani 1 1 d D . .
N2 N 0.1179(4) -0.2734(8) 0.2345(3) 0.0331(14) Uani 1 1 d . . .
N3 N 0.1387(6) -0.8625(10) 0.5369(4) 0.0500(18) Uani 1 1 d . . .
O1 O 0.3378(5) 0.2807(7) 0.2291(4) 0.0522(16) Uani 1 1 d . . .
O2 O 0.4508(4) -0.3545(7) 0.1666(4) 0.0519(16) Uani 1 1 d . . .
O3 O 0.0635(6) -0.7580(11) 0.4344(4) 0.077(2) Uani 1 1 d . . .
Cl1 Cl 0.23661(16) 0.0300(3) 0.31205(12) 0.0470(5) Uani 1 1 d . . .
Cl2 Cl -0.20541(19) -0.6283(4) 0.44353(13) 0.0626(6) Uani 1 1 d . . .
S1 S 0.16727(15) -0.4789(3) 0.33670(11) 0.0377(4) Uani 1 1 d . . .
Hg1 Hg -0.07478(2) -0.54563(4) 0.373687(17) 0.03915(12) Uani 1 1 d . . .
H1A H 0.328(5) -0.413(6) 0.236(4) 0.03(2) Uiso 1 1 d 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
C1 C2 1.358(12) . ?
C1 C6 1.405(10) . ?
C1 H1 0.9300 . ?
C2 C3 1.359(13) . ?
C2 H2 0.9300 . ?
C3 C4 1.383(12) . ?
C3 H3 0.9300 . ?
C4 C5 1.405(10) . ?
C4 H4 0.9300 . ?
C5 C6 1.383(10) . ?
C5 C10 1.460(10) . ?
C6 C7 1.453(10) . ?
C7 O2 1.207(9) . ?
C7 C8 1.508(9) . ?
C8 C9 1.345(10) . ?
C8 N1 1.355(9) . ?
C9 C10 1.470(10) . ?
C9 Cl1 1.716(7) . ?
C10 O1 1.222(9) . ?
C11 N2 1.289(9) . ?
C11 N1 1.389(9) . ?
C11 S1 1.701(7) . ?
C12 C13 1.309(10) . ?
C12 S1 1.699(7) . ?
C12 Hg1 2.063(7) . ?
C13 N2 1.370(9) . ?
C13 H13 0.9300 . ?
C14 N3 1.423(13) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 N3 1.429(12) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 O3 1.203(12) . ?
C16 N3 1.313(12) . ?
C16 H16 0.9300 . ?
N1 H1A 0.84(2) . ?
O3 Hg1 2.623(7) . ?
Cl2 Hg1 2.300(2) . ?

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 C1 C6 120.4(8) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C1 C2 C3 120.2(8) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C2 C3 C4 121.6(8) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C3 C4 C5 118.7(8) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C6 C5 C4 119.7(7) . . ?
C6 C5 C10 120.7(6) . . ?
C4 C5 C10 119.5(7) . . ?
C5 C6 C1 119.3(7) . . ?
C5 C6 C7 121.0(7) . . ?
C1 C6 C7 119.5(7) . . ?
O2 C7 C6 123.4(7) . . ?
O2 C7 C8 118.5(6) . . ?
C6 C7 C8 118.1(6) . . ?
C9 C8 N1 128.2(6) . . ?
C9 C8 C7 119.1(6) . . ?
N1 C8 C7 112.6(6) . . ?
C8 C9 C10 122.7(6) . . ?
C8 C9 Cl1 122.2(6) . . ?
C10 C9 Cl1 115.1(5) . . ?
O1 C10 C5 121.9(7) . . ?
O1 C10 C9 120.5(7) . . ?
C5 C10 C9 117.6(6) . . ?
N2 C11 N1 123.3(6) . . ?
N2 C11 S1 114.8(5) . . ?
N1 C11 S1 121.9(5) . . ?
C13 C12 S1 109.4(5) . . ?
C13 C12 Hg1 128.7(6) . . ?
S1 C12 Hg1 121.9(4) . . ?
C12 C13 N2 117.2(7) . . ?
C12 C13 H13 121.4 . . ?
N2 C13 H13 121.4 . . ?
N3 C14 H14A 109.5 . . ?
N3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N3 C15 H15A 109.5 . . ?
N3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O3 C16 N3 124.5(10) . . ?
O3 C16 H16 117.8 . . ?
N3 C16 H16 117.8 . . ?
C8 N1 C11 126.3(6) . . ?
C8 N1 H1A 113(5) . . ?
C11 N1 H1A 116(5) . . ?
C11 N2 C13 109.2(6) . . ?
C16 N3 C14 120.9(9) . . ?
C16 N3 C15 122.9(9) . . ?
C14 N3 C15 116.1(9) . . ?
C16 O3 Hg1 120.7(7) . . ?
C12 S1 C11 89.5(3) . . ?
C12 Hg1 Cl2 170.1(2) . . ?
C12 Hg1 O3 89.9(3) . . ?
Cl2 Hg1 O3 94.86(18) . . ?

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 C1 C2 C3 0.3(13) . . . . ?
C1 C2 C3 C4 1.2(14) . . . . ?
C2 C3 C4 C5 -2.4(13) . . . . ?
C3 C4 C5 C6 2.1(11) . . . . ?
C3 C4 C5 C10 178.4(7) . . . . ?
C4 C5 C6 C1 -0.6(11) . . . . ?
C10 C5 C6 C1 -176.9(7) . . . . ?
C4 C5 C6 C7 -177.3(7) . . . . ?
C10 C5 C6 C7 6.4(11) . . . . ?
C2 C1 C6 C5 -0.6(12) . . . . ?
C2 C1 C6 C7 176.2(7) . . . . ?
C5 C6 C7 O2 179.8(8) . . . . ?
C1 C6 C7 O2 3.1(12) . . . . ?
C5 C6 C7 C8 -2.1(10) . . . . ?
C1 C6 C7 C8 -178.7(7) . . . . ?
O2 C7 C8 C9 172.6(7) . . . . ?
C6 C7 C8 C9 -5.6(10) . . . . ?
O2 C7 C8 N1 -3.9(10) . . . . ?
C6 C7 C8 N1 177.9(6) . . . . ?
N1 C8 C9 C10 -175.3(7) . . . . ?
C7 C8 C9 C10 8.8(10) . . . . ?
N1 C8 C9 Cl1 5.4(11) . . . . ?
C7 C8 C9 Cl1 -170.5(5) . . . . ?
C6 C5 C10 O1 176.7(7) . . . . ?
C4 C5 C10 O1 0.4(11) . . . . ?
C6 C5 C10 C9 -3.4(10) . . . . ?
C4 C5 C10 C9 -179.7(7) . . . . ?
C8 C9 C10 O1 175.4(7) . . . . ?
Cl1 C9 C10 O1 -5.2(9) . . . . ?
C8 C9 C10 C5 -4.5(10) . . . . ?
Cl1 C9 C10 C5 174.8(5) . . . . ?
S1 C12 C13 N2 1.5(9) . . . . ?
Hg1 C12 C13 N2 -175.1(5) . . . . ?
C9 C8 N1 C11 33.5(12) . . . . ?
C7 C8 N1 C11 -150.3(7) . . . . ?
N2 C11 N1 C8 36.8(11) . . . . ?
S1 C11 N1 C8 -143.4(6) . . . . ?
N1 C11 N2 C13 -179.7(7) . . . . ?
S1 C11 N2 C13 0.5(8) . . . . ?
C12 C13 N2 C11 -1.3(10) . . . . ?
O3 C16 N3 C14 4.4(16) . . . . ?
O3 C16 N3 C15 -176.7(10) . . . . ?
N3 C16 O3 Hg1 -158.7(7) . . . . ?
C13 C12 S1 C11 -0.9(6) . . . . ?
Hg1 C12 S1 C11 175.9(5) . . . . ?
N2 C11 S1 C12 0.2(6) . . . . ?
N1 C11 S1 C12 -179.6(6) . . . . ?
C13 C12 Hg1 Cl2 -73.4(15) . . . . ?
S1 C12 Hg1 Cl2 110.4(12) . . . . ?
C13 C12 Hg1 O3 167.9(7) . . . . ?
S1 C12 Hg1 O3 -8.3(5) . . . . ?
C16 O3 Hg1 C12 142.3(8) . . . . ?
C16 O3 Hg1 Cl2 -29.0(8) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C14 H14C Cl1 0.96 2.93 3.787(14) 149.1 1_545
C15 H15B O3 0.96 2.65 3.580(14) 162.4 3_536
N1 H1A O1 0.84(2) 2.39(4) 3.136(8) 149(7) 1_545
N1 H1A O2 0.84(2) 2.17(7) 2.612(8) 113(6) .

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.765
_refine_diff_density_min         -0.942
_refine_diff_density_rms         0.138
