# Electronic Supplementary Material (ESI) for ChemComm.
# 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/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_f:\1\exp852~1\olex2_~1\exp_8520
_database_code_depnum_ccdc_archive 'CCDC 1054664'
_audit_update_record             
;
2015-03-18 deposited with the CCDC.
2015-07-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H16 Cl2 Hg N2 S2'
_chemical_formula_weight         595.94

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Hg Hg -4.2923 7.6849 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_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                   26.6229(4)
_cell_length_b                   10.0005(2)
_cell_length_c                   13.9461(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.4140(10)
_cell_angle_gamma                90.00
_cell_volume                     3706.45(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4754
_cell_measurement_theta_min      3.1560
_cell_measurement_theta_max      73.3550

_exptl_crystal_description       rodlike
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.136
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2272
_exptl_absorpt_coefficient_mu    19.683
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.27661
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
'CrysAlisPro, Agilent Technologies,Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7098
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_sigmaI/netI    0.0364
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.33
_diffrn_reflns_theta_max         73.50
_reflns_number_total             3614
_reflns_number_gt                3319
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'CrysAlisPro, Agilent Technologies,Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)'
_computing_cell_refinement       
'CrysAlisPro, Agilent Technologies,Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)'
_computing_data_reduction        
'CrysAlisPro, Agilent Technologies,Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL

_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)+(0.0627P)²+0.0000P] 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         3614
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_ref         0.0967
_refine_ls_wR_factor_gt          0.0940
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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
Hg1 Hg 0.411892(7) 0.71792(2) 0.086094(14) 0.01889(10) Uani 1 1 d . . .
Cl2 Cl 0.46913(5) 0.89971(13) 0.09536(9) 0.0227(3) Uani 1 1 d . . .
S2 S 0.42741(5) 0.82212(13) 0.83239(9) 0.0197(3) Uani 1 1 d . . .
S1 S 0.31940(5) 0.77398(13) 0.53978(9) 0.0197(3) Uani 1 1 d . . .
Cl1 Cl 0.33981(5) 0.60856(15) 0.01494(9) 0.0278(3) Uani 1 1 d . . .
N1 N 0.38370(17) 0.7326(4) 0.2475(3) 0.0191(9) Uani 1 1 d . . .
C12 C 0.32451(18) 0.9408(5) 0.6889(4) 0.0186(10) Uani 1 1 d . . .
C14 C 0.34697(18) 0.7614(5) 0.4297(4) 0.0168(10) Uani 1 1 d . . .
C15 C 0.38749(17) 0.8381(5) 0.4024(3) 0.0165(10) Uani 1 1 d . . .
H13 H 0.4035 0.9004 0.4455 0.020 Uiso 1 1 calc R . .
C18 C 0.32623(18) 0.6682(5) 0.3638(4) 0.0201(10) Uani 1 1 d . . .
H15 H 0.2992 0.6125 0.3806 0.024 Uiso 1 1 calc R . .
C9 C 0.2671(2) 0.9937(6) 0.8465(4) 0.0275(12) Uani 1 1 d . . .
H8 H 0.2476 1.0117 0.9000 0.033 Uiso 1 1 calc R . .
C1 C 0.54710(18) 0.5978(5) 0.9127(3) 0.0189(10) Uani 1 1 d . . .
H1 H 0.5805 0.6145 0.9378 0.023 Uiso 1 1 calc R . .
C3 C 0.46598(18) 0.6830(5) 0.8559(3) 0.0146(9) Uani 1 1 d . . .
C11 C 0.28943(19) 1.0456(5) 0.6871(4) 0.0249(11) Uani 1 1 d . . .
H10 H 0.2851 1.0996 0.6311 0.030 Uiso 1 1 calc R . .
C2 C 0.5155(2) 0.7061(5) 0.8943(4) 0.0189(11) Uani 1 1 d . . .
H2 H 0.5269 0.7946 0.9074 0.023 Uiso 1 1 calc R . .
C16 C 0.40370(18) 0.8209(6) 0.3107(4) 0.0187(10) Uani 1 1 d . . .
H14 H 0.4306 0.8752 0.2916 0.022 Uiso 1 1 calc R . .
C5 C 0.48598(18) 0.4489(5) 0.8617(3) 0.0180(10) Uani 1 1 d . . .
H3 H 0.4755 0.3592 0.8507 0.022 Uiso 1 1 calc R . .
C4 C 0.45160(19) 0.5505(5) 0.8404(3) 0.0199(10) Uani 1 1 d . . .
H4 H 0.4185 0.5298 0.8155 0.024 Uiso 1 1 calc R . .
C17 C 0.34507(19) 0.6577(5) 0.2754(4) 0.0200(10) Uani 1 1 d . . .
H16 H 0.3303 0.5947 0.2312 0.024 Uiso 1 1 calc R . .
C13 C 0.35243(19) 0.9117(5) 0.6010(4) 0.0205(10) Uani 1 1 d . . .
H11 H 0.3877 0.8863 0.6191 0.025 Uiso 1 1 calc R . .
H12 H 0.3526 0.9913 0.5589 0.025 Uiso 1 1 calc R . .
C6 C 0.36865(19) 0.7497(6) 0.7828(4) 0.0195(10) Uani 1 1 d . . .
H5 H 0.3736 0.7087 0.7195 0.023 Uiso 1 1 calc R . .
H6 H 0.3568 0.6797 0.8263 0.023 Uiso 1 1 calc R . .
C8 C 0.30125(19) 0.8896(6) 0.8505(4) 0.0224(11) Uani 1 1 d . . .
H7 H 0.3050 0.8361 0.9067 0.027 Uiso 1 1 calc R . .
C7 C 0.33038(18) 0.8624(5) 0.7724(4) 0.0182(10) Uani 1 1 d . . .
C10 C 0.2611(2) 1.0721(6) 0.7644(4) 0.0271(12) Uani 1 1 d . . .
H9 H 0.2376 1.1437 0.7615 0.032 Uiso 1 1 calc R . .
N2 N 0.53294(15) 0.4706(4) 0.8969(3) 0.0163(8) Uani 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
Hg1 Cl2 2.3708(12) . ?
Hg1 Cl1 2.3741(13) . ?
Hg1 N2 2.393(4) 5_666 ?
Hg1 N1 2.420(5) . ?
S2 C3 1.749(5) . ?
S2 C6 1.822(5) . ?
S1 C14 1.746(5) . ?
S1 C13 1.819(5) . ?
N1 C16 1.335(7) . ?
N1 C17 1.348(7) . ?
C12 C11 1.403(7) . ?
C12 C7 1.405(7) . ?
C12 C13 1.499(7) . ?
C14 C15 1.395(7) . ?
C14 C18 1.399(7) . ?
C15 C16 1.384(7) . ?
C18 C17 1.363(8) . ?
C9 C8 1.382(8) . ?
C9 C10 1.389(8) . ?
C1 N2 1.341(7) . ?
C1 C2 1.387(7) . ?
C3 C4 1.392(7) . ?
C3 C2 1.411(7) . ?
C11 C10 1.378(8) . ?
C5 N2 1.333(6) . ?
C5 C4 1.388(7) . ?
C6 C7 1.521(7) . ?
C8 C7 1.401(7) . ?
N2 Hg1 2.393(4) 5_666 ?

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
Cl2 Hg1 Cl1 151.28(5) . . ?
Cl2 Hg1 N2 102.12(11) . 5_666 ?
Cl1 Hg1 N2 98.90(10) . 5_666 ?
Cl2 Hg1 N1 97.85(11) . . ?
Cl1 Hg1 N1 97.42(11) . . ?
N2 Hg1 N1 100.25(14) 5_666 . ?
C3 S2 C6 103.7(3) . . ?
C14 S1 C13 104.5(2) . . ?
C16 N1 C17 117.3(5) . . ?
C16 N1 Hg1 121.4(4) . . ?
C17 N1 Hg1 121.2(4) . . ?
C11 C12 C7 118.2(5) . . ?
C11 C12 C13 119.5(5) . . ?
C7 C12 C13 122.3(5) . . ?
C15 C14 C18 117.9(5) . . ?
C15 C14 S1 125.0(4) . . ?
C18 C14 S1 117.1(4) . . ?
C16 C15 C14 118.2(5) . . ?
C17 C18 C14 119.5(5) . . ?
C8 C9 C10 120.1(5) . . ?
N2 C1 C2 123.3(5) . . ?
C4 C3 C2 117.2(5) . . ?
C4 C3 S2 125.1(4) . . ?
C2 C3 S2 117.7(4) . . ?
C10 C11 C12 121.6(5) . . ?
C1 C2 C3 119.0(5) . . ?
N1 C16 C15 123.9(5) . . ?
N2 C5 C4 123.5(5) . . ?
C5 C4 C3 119.4(4) . . ?
N1 C17 C18 123.1(5) . . ?
C12 C13 S1 106.3(3) . . ?
C7 C6 S2 107.3(4) . . ?
C9 C8 C7 120.6(5) . . ?
C8 C7 C12 119.8(5) . . ?
C8 C7 C6 117.9(5) . . ?
C12 C7 C6 122.2(5) . . ?
C11 C10 C9 119.7(5) . . ?
C5 N2 C1 117.6(5) . . ?
C5 N2 Hg1 117.7(3) . 5_666 ?
C1 N2 Hg1 124.5(3) . 5_666 ?

_diffrn_measured_fraction_theta_max 0.967
_diffrn_reflns_theta_full        73.50
_diffrn_measured_fraction_theta_full 0.967
_refine_diff_density_max         2.759
_refine_diff_density_min         -1.798
_refine_diff_density_rms         0.184

####################################################################### 
# 
# 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_f:\1\exp810~1\olex2_~1\exp_8106
_database_code_depnum_ccdc_archive 'CCDC 1054665'
_audit_update_record             
;
2015-03-18 deposited with the CCDC.
2015-07-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H19 Ag F3 N2 O3 S3'
_chemical_formula_weight         584.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Ag Ag 0.1306 4.2820 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_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                   23.7546(4)
_cell_length_b                   9.6388(2)
_cell_length_c                   18.5295(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.688(2)
_cell_angle_gamma                90.00
_cell_volume                     4233.84(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4334
_cell_measurement_theta_min      4.7680
_cell_measurement_theta_max      73.3020

_exptl_crystal_description       rodlike
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.834
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2344
_exptl_absorpt_coefficient_mu    10.880
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.50370
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
'CrysAlisPro, Agilent Technologies,Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8289
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_sigmaI/netI    0.0315
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.73
_diffrn_reflns_theta_max         73.43
_reflns_number_total             4145
_reflns_number_gt                3616
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'CrysAlisPro, Agilent Technologies,Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)'
_computing_cell_refinement       
'CrysAlisPro, Agilent Technologies,Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)'
_computing_data_reduction        
'CrysAlisPro, Agilent Technologies,Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL

_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)+(0.0356P)²+5.4339P] 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         4145
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0280
_refine_ls_wR_factor_ref         0.0722
_refine_ls_wR_factor_gt          0.0676
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.002
_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
Ag1 Ag 0.449019(8) 0.47131(2) 0.440113(11) 0.02344(8) Uani 1 1 d . . .
S3 S 0.42202(3) 0.81977(7) 0.40945(3) 0.01667(14) Uani 1 1 d . . .
S1 S 0.22961(3) 0.39906(7) 0.64530(4) 0.02170(15) Uani 1 1 d . . .
S2 S 0.35458(3) 0.59814(8) 0.79898(4) 0.02254(15) Uani 1 1 d . . .
N1 N 0.37756(10) 0.4553(3) 0.50349(13) 0.0208(5) Uani 1 1 d . . .
N2 N 0.48328(10) 0.5450(3) 0.62916(13) 0.0207(5) Uani 1 1 d . . .
F2 F 0.49976(9) 1.0052(2) 0.39300(18) 0.0616(8) Uani 1 1 d . . .
O3 O 0.46028(9) 0.7535(2) 0.46246(12) 0.0280(5) Uani 1 1 d . . .
F1 F 0.41578(9) 1.0720(2) 0.35788(15) 0.0521(7) Uani 1 1 d . . .
O2 O 0.36455(8) 0.8300(2) 0.42899(11) 0.0255(4) Uani 1 1 d . . .
O1 O 0.42813(10) 0.7760(3) 0.33615(12) 0.0343(5) Uani 1 1 d . . .
C11 C 0.35718(12) 0.5652(3) 0.53851(15) 0.0202(6) Uani 1 1 d . . .
H10 H 0.3750 0.6525 0.5334 0.024 Uiso 1 1 calc R . .
C6 C 0.21445(12) 0.5149(3) 0.77734(14) 0.0170(5) Uani 1 1 d . . .
F3 F 0.44064(11) 1.0602(3) 0.47142(17) 0.0674(9) Uani 1 1 d . . .
C8 C 0.31589(12) 0.4339(3) 0.80030(16) 0.0217(6) Uani 1 1 d . . .
H7 H 0.3135 0.3922 0.7514 0.026 Uiso 1 1 calc R . .
H8 H 0.3362 0.3682 0.8338 0.026 Uiso 1 1 calc R . .
C17 C 0.45978(12) 0.4333(3) 0.65842(16) 0.0222(6) Uani 1 1 d . . .
H15 H 0.4709 0.3441 0.6427 0.027 Uiso 1 1 calc R . .
C5 C 0.25723(11) 0.4589(3) 0.82441(15) 0.0182(5) Uani 1 1 d . . .
C10 C 0.31183(12) 0.5578(3) 0.58134(14) 0.0190(5) Uani 1 1 d . . .
H9 H 0.2987 0.6388 0.6042 0.023 Uiso 1 1 calc R . .
C3 C 0.19136(13) 0.4408(3) 0.91823(15) 0.0261(6) Uani 1 1 d . . .
H2 H 0.1836 0.4153 0.9661 0.031 Uiso 1 1 calc R . .
C1 C 0.16064(12) 0.5335(3) 0.80202(16) 0.0228(6) Uani 1 1 d . . .
H4 H 0.1315 0.5720 0.7706 0.027 Uiso 1 1 calc R . .
C16 C 0.46625(13) 0.6701(3) 0.65222(17) 0.0261(6) Uani 1 1 d . . .
H14 H 0.4818 0.7507 0.6318 0.031 Uiso 1 1 calc R . .
C9 C 0.28543(11) 0.4305(3) 0.59076(14) 0.0171(5) Uani 1 1 d . . .
C12 C 0.35080(12) 0.3327(3) 0.51123(16) 0.0239(6) Uani 1 1 d . . .
H11 H 0.3636 0.2543 0.4859 0.029 Uiso 1 1 calc R . .
C18 C 0.42063(12) 0.4405(3) 0.70968(15) 0.0216(6) Uani 1 1 d . . .
H16 H 0.4053 0.3582 0.7287 0.026 Uiso 1 1 calc R . .
C13 C 0.30604(12) 0.3163(3) 0.55394(15) 0.0223(6) Uani 1 1 d . . .
H12 H 0.2891 0.2276 0.5585 0.027 Uiso 1 1 calc R . .
C15 C 0.42759(13) 0.6874(3) 0.70366(17) 0.0255(6) Uani 1 1 d . . .
H13 H 0.4173 0.7776 0.7186 0.031 Uiso 1 1 calc R . .
C2 C 0.14924(13) 0.4964(3) 0.87220(17) 0.0269(7) Uani 1 1 d . . .
H3 H 0.1125 0.5093 0.8884 0.032 Uiso 1 1 calc R . .
C14 C 0.40379(11) 0.5701(3) 0.73344(15) 0.0191(5) Uani 1 1 d . . .
C4 C 0.24489(13) 0.4222(3) 0.89453(15) 0.0231(6) Uani 1 1 d . . .
H1 H 0.2737 0.3838 0.9265 0.028 Uiso 1 1 calc R . .
C7 C 0.22543(12) 0.5558(3) 0.70095(15) 0.0199(5) Uani 1 1 d . . .
H6 H 0.2613 0.6081 0.7007 0.024 Uiso 1 1 calc R . .
H5 H 0.1946 0.6163 0.6808 0.024 Uiso 1 1 calc R . .
C19 C 0.44589(14) 0.9983(3) 0.4085(2) 0.0363(8) Uani 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
Ag1 N2 2.127(2) 5_666 ?
Ag1 N1 2.131(2) . ?
Ag1 Ag1 3.2259(4) 5_666 ?
S3 O2 1.438(2) . ?
S3 O1 1.438(2) . ?
S3 O3 1.444(2) . ?
S3 C19 1.813(3) . ?
S1 C9 1.745(3) . ?
S1 C7 1.835(3) . ?
S2 C14 1.760(3) . ?
S2 C8 1.832(3) . ?
N1 C11 1.348(4) . ?
N1 C12 1.353(4) . ?
N2 C17 1.343(4) . ?
N2 C16 1.349(4) . ?
N2 Ag1 2.127(2) 5_666 ?
F2 C19 1.331(4) . ?
F1 C19 1.345(4) . ?
C11 C10 1.380(4) . ?
C6 C1 1.397(4) . ?
C6 C5 1.404(4) . ?
C6 C7 1.508(4) . ?
F3 C19 1.323(5) . ?
C8 C5 1.510(4) . ?
C17 C18 1.373(4) . ?
C5 C4 1.396(4) . ?
C10 C9 1.394(4) . ?
C3 C2 1.381(5) . ?
C3 C4 1.383(4) . ?
C1 C2 1.392(4) . ?
C16 C15 1.375(4) . ?
C9 C13 1.400(4) . ?
C12 C13 1.375(4) . ?
C18 C14 1.392(4) . ?
C15 C14 1.393(4) . ?

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
N2 Ag1 N1 170.82(10) 5_666 . ?
N2 Ag1 Ag1 82.21(7) 5_666 5_666 ?
N1 Ag1 Ag1 102.87(6) . 5_666 ?
O2 S3 O1 114.39(13) . . ?
O2 S3 O3 115.17(13) . . ?
O1 S3 O3 114.54(14) . . ?
O2 S3 C19 103.89(15) . . ?
O1 S3 C19 102.62(18) . . ?
O3 S3 C19 104.08(15) . . ?
C9 S1 C7 104.65(14) . . ?
C14 S2 C8 103.45(14) . . ?
C11 N1 C12 116.7(2) . . ?
C11 N1 Ag1 122.1(2) . . ?
C12 N1 Ag1 121.2(2) . . ?
C17 N2 C16 116.6(2) . . ?
C17 N2 Ag1 122.3(2) . 5_666 ?
C16 N2 Ag1 120.72(19) . 5_666 ?
N1 C11 C10 123.6(3) . . ?
C1 C6 C5 119.2(3) . . ?
C1 C6 C7 119.4(3) . . ?
C5 C6 C7 121.4(2) . . ?
C5 C8 S2 109.8(2) . . ?
N2 C17 C18 123.8(3) . . ?
C4 C5 C6 119.3(3) . . ?
C4 C5 C8 119.2(3) . . ?
C6 C5 C8 121.5(3) . . ?
C11 C10 C9 119.4(3) . . ?
C2 C3 C4 119.9(3) . . ?
C2 C1 C6 120.7(3) . . ?
N2 C16 C15 123.7(3) . . ?
C10 C9 C13 117.2(2) . . ?
C10 C9 S1 126.2(2) . . ?
C13 C9 S1 116.6(2) . . ?
N1 C12 C13 123.2(3) . . ?
C17 C18 C14 119.0(3) . . ?
C12 C13 C9 119.8(3) . . ?
C16 C15 C14 118.8(3) . . ?
C3 C2 C1 120.0(3) . . ?
C18 C14 C15 118.1(3) . . ?
C18 C14 S2 125.0(2) . . ?
C15 C14 S2 117.0(2) . . ?
C3 C4 C5 121.0(3) . . ?
C6 C7 S1 109.34(19) . . ?
F3 C19 F2 108.3(3) . . ?
F3 C19 F1 107.5(3) . . ?
F2 C19 F1 107.4(3) . . ?
F3 C19 S3 111.8(3) . . ?
F2 C19 S3 110.8(2) . . ?
F1 C19 S3 110.8(2) . . ?

_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_theta_full        73.43
_diffrn_measured_fraction_theta_full 0.976
_refine_diff_density_max         1.061
_refine_diff_density_min         -0.491
_refine_diff_density_rms         0.083
####################################################################### 
# 
# 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_f:\\struct~1\olex2_~1\exp_9683
_database_code_depnum_ccdc_archive 'CCDC 1054666'
_audit_update_record             
;
2015-03-18 deposited with the CCDC.
2015-07-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H19 Cl2 N3 S2 Zn'
_chemical_formula_weight         501.77

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'
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'
Cl Cl 0.1484 0.1585 '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                   8.5494(2)
_cell_length_b                   18.8079(4)
_cell_length_c                   13.9638(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.017(2)
_cell_angle_gamma                90.00
_cell_volume                     2217.58(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6942
_cell_measurement_theta_min      3.6660
_cell_measurement_theta_max      28.9900

_exptl_crystal_description       rodlike
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1024
_exptl_absorpt_coefficient_mu    1.548
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.75248
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
'CrysAlisPro, Agilent Technologies,Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  'SuperNova, Dual, Mo at zero, Atlas'
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11948
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_sigmaI/netI    0.0272
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.84
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3898
_reflns_number_gt                3495
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'CrysAlisPro, Agilent Technologies,Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)'
_computing_cell_refinement       
'CrysAlisPro, Agilent Technologies,Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)'
_computing_data_reduction        
'CrysAlisPro, Agilent Technologies,Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL

_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)+(0.0313P)²+1.4149P] 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         3898
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0290
_refine_ls_wR_factor_ref         0.0722
_refine_ls_wR_factor_gt          0.0694
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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
Zn1 Zn 0.26293(3) 0.610621(14) 0.840943(18) 0.02664(10) Uani 1 1 d . . .
Cl2 Cl 0.40320(7) 0.70951(3) 0.87701(4) 0.03268(15) Uani 1 1 d . . .
Cl1 Cl 0.04843(7) 0.57928(3) 0.90346(4) 0.03141(15) Uani 1 1 d . . .
S1 S 0.74881(7) 0.33979(3) 0.86338(4) 0.02987(15) Uani 1 1 d . . .
S2 S 1.06394(8) 0.37035(3) 0.61758(4) 0.03689(17) Uani 1 1 d . . .
N2 N 0.8213(2) 0.38831(10) 0.30511(13) 0.0283(4) Uani 1 1 d . . .
N1 N 0.4185(2) 0.52820(10) 0.86321(13) 0.0273(4) Uani 1 1 d . . .
C4 C 0.6289(3) 0.41442(12) 0.86636(15) 0.0264(5) Uani 1 1 d . . .
C14 C 0.9607(3) 0.37595(12) 0.49930(16) 0.0311(6) Uani 1 1 d . . .
C7 C 1.0563(3) 0.31697(12) 0.84995(16) 0.0256(5) Uani 1 1 d . . .
C15 C 1.0194(3) 0.42325(13) 0.43706(17) 0.0387(6) Uani 1 1 d . . .
H14 H 1.1079 0.4525 0.4602 0.046 Uiso 1 1 calc R . .
C13 C 0.9736(3) 0.29489(12) 0.66946(16) 0.0309(5) Uani 1 1 d . . .
H11 H 0.8638 0.3066 0.6782 0.037 Uiso 1 1 calc R . .
H12 H 0.9705 0.2532 0.6259 0.037 Uiso 1 1 calc R . .
C17 C 0.8283(3) 0.33601(13) 0.46229(16) 0.0306(5) Uani 1 1 d . . .
H13 H 0.7832 0.3038 0.5027 0.037 Uiso 1 1 calc R . .
C6 C 0.9406(3) 0.37724(12) 0.84909(16) 0.0268(5) Uani 1 1 d . . .
H6 H 0.9320 0.4036 0.7871 0.032 Uiso 1 1 calc R . .
H5 H 0.9771 0.4106 0.9028 0.032 Uiso 1 1 calc R . .
C16 C 0.9484(3) 0.42732(13) 0.34182(17) 0.0365(6) Uani 1 1 d . . .
H15 H 0.9912 0.4592 0.3000 0.044 Uiso 1 1 calc R . .
C18 C 0.7633(3) 0.34382(13) 0.36576(16) 0.0307(5) Uani 1 1 d . . .
H16 H 0.6728 0.3162 0.3412 0.037 Uiso 1 1 calc R . .
C10 C 1.2758(3) 0.20659(14) 0.8596(2) 0.0436(7) Uani 1 1 d . . .
H9 H 1.3506 0.1690 0.8627 0.052 Uiso 1 1 calc R . .
C8 C 1.1505(3) 0.29891(13) 0.93752(17) 0.0305(5) Uani 1 1 d . . .
H7 H 1.1399 0.3247 0.9947 0.037 Uiso 1 1 calc R . .
C12 C 1.0727(3) 0.27854(12) 0.76601(16) 0.0282(5) Uani 1 1 d . . .
C5 C 0.4681(3) 0.40325(13) 0.86664(19) 0.0358(6) Uani 1 1 d . . .
H4 H 0.4274 0.3563 0.8676 0.043 Uiso 1 1 calc R . .
C2 C 0.5742(3) 0.53870(13) 0.86581(16) 0.0305(5) Uani 1 1 d . . .
H1 H 0.6121 0.5862 0.8665 0.037 Uiso 1 1 calc R . .
C3 C 0.6820(3) 0.48428(13) 0.86757(16) 0.0305(5) Uani 1 1 d . . .
H3 H 0.7914 0.4943 0.8696 0.037 Uiso 1 1 calc R . .
C9 C 1.2587(3) 0.24411(13) 0.94214(19) 0.0385(6) Uani 1 1 d . . .
H8 H 1.3216 0.2322 1.0023 0.046 Uiso 1 1 calc R . .
C1 C 0.3690(3) 0.46053(13) 0.86559(18) 0.0359(6) Uani 1 1 d . . .
H2 H 0.2598 0.4520 0.8666 0.043 Uiso 1 1 calc R . .
C11 C 1.1835(3) 0.22390(13) 0.77181(19) 0.0396(6) Uani 1 1 d . . .
H10 H 1.1962 0.1981 0.7150 0.047 Uiso 1 1 calc R . .
C20 C 0.4970(6) 0.60110(17) 0.3947(2) 0.0734(12) Uani 1 1 d . . .
H19 H 0.4236 0.6331 0.3544 0.110 Uiso 1 1 calc R . .
H18 H 0.6006 0.6026 0.3730 0.110 Uiso 1 1 calc R . .
H17 H 0.5083 0.6162 0.4626 0.110 Uiso 1 1 calc R . .
C19 C 0.4411(7) 0.5354(3) 0.3866(2) 0.1058(19) Uani 1 1 d . . .
N3 N 0.4661(11) 0.4656(3) 0.3755(4) 0.085(2) Uani 0.50 1 d P . .
N4 N 0.3084(12) 0.5088(6) 0.3851(5) 0.138(4) Uani 0.50 1 d P . .


_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 N1 2.0346(19) . ?
Zn1 N2 2.0537(19) 3_666 ?
Zn1 Cl2 2.2275(6) . ?
Zn1 Cl1 2.2303(6) . ?
S1 C4 1.742(2) . ?
S1 C6 1.824(2) . ?
S2 C14 1.750(2) . ?
S2 C13 1.820(2) . ?
N2 C18 1.340(3) . ?
N2 C16 1.344(3) . ?
N2 Zn1 2.0537(19) 3_666 ?
N1 C2 1.341(3) . ?
N1 C1 1.343(3) . ?
C4 C3 1.389(3) . ?
C4 C5 1.392(3) . ?
C14 C17 1.389(3) . ?
C14 C15 1.391(4) . ?
C7 C8 1.397(3) . ?
C7 C12 1.403(3) . ?
C7 C6 1.503(3) . ?
C15 C16 1.375(3) . ?
C13 C12 1.507(3) . ?
C17 C18 1.383(3) . ?
C10 C9 1.379(4) . ?
C10 C11 1.388(4) . ?
C8 C9 1.380(4) . ?
C12 C11 1.392(3) . ?
C5 C1 1.369(4) . ?
C2 C3 1.375(3) . ?
C20 C19 1.323(5) . ?
C19 N4 1.237(8) . ?
C19 N3 1.344(7) . ?
N3 N4 1.599(13) . ?

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
N1 Zn1 N2 106.15(7) . 3_666 ?
N1 Zn1 Cl2 106.60(6) . . ?
N2 Zn1 Cl2 107.99(6) 3_666 . ?
N1 Zn1 Cl1 107.27(5) . . ?
N2 Zn1 Cl1 102.10(6) 3_666 . ?
Cl2 Zn1 Cl1 125.37(2) . . ?
C4 S1 C6 103.52(11) . . ?
C14 S2 C13 103.89(11) . . ?
C18 N2 C16 117.2(2) . . ?
C18 N2 Zn1 121.80(16) . 3_666 ?
C16 N2 Zn1 120.66(16) . 3_666 ?
C2 N1 C1 117.0(2) . . ?
C2 N1 Zn1 120.97(16) . . ?
C1 N1 Zn1 121.63(16) . . ?
C3 C4 C5 117.6(2) . . ?
C3 C4 S1 124.75(18) . . ?
C5 C4 S1 117.62(18) . . ?
C17 C14 C15 117.8(2) . . ?
C17 C14 S2 125.43(19) . . ?
C15 C14 S2 116.77(19) . . ?
C8 C7 C12 119.1(2) . . ?
C8 C7 C6 118.6(2) . . ?
C12 C7 C6 122.27(19) . . ?
C16 C15 C14 119.5(2) . . ?
C12 C13 S2 107.53(16) . . ?
C18 C17 C14 119.0(2) . . ?
C7 C6 S1 108.02(15) . . ?
N2 C16 C15 123.1(2) . . ?
N2 C18 C17 123.4(2) . . ?
C9 C10 C11 119.9(2) . . ?
C9 C8 C7 120.9(2) . . ?
C11 C12 C7 119.2(2) . . ?
C11 C12 C13 119.0(2) . . ?
C7 C12 C13 121.8(2) . . ?
C1 C5 C4 119.4(2) . . ?
N1 C2 C3 123.4(2) . . ?
C2 C3 C4 119.2(2) . . ?
C10 C9 C8 120.1(2) . . ?
N1 C1 C5 123.3(2) . . ?
C10 C11 C12 120.8(2) . . ?
N4 C19 C20 134.2(9) . . ?
N4 C19 N3 76.4(6) . . ?
C20 C19 N3 149.4(7) . . ?
C19 N3 N4 48.8(4) . . ?
C19 N4 N3 54.8(5) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.471
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.058
####################################################################### 
# 
# 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_f:\\exp818~1\olex2_~1\exp_8184
_database_code_depnum_ccdc_archive 'CCDC 1058370'
_audit_update_record             
;
2015-04-08 deposited with the CCDC.
2015-07-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H12 Hg I2 N2 S2'
_chemical_formula_weight         774.81

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Hg Hg -4.2923 7.6849 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_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                   26.4973(8)
_cell_length_b                   10.4756(3)
_cell_length_c                   14.4782(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.642(3)
_cell_angle_gamma                90.00
_cell_volume                     4005.6(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3985
_cell_measurement_theta_min      4.5250
_cell_measurement_theta_max      73.0950

_exptl_crystal_description       rodlike
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.570
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2816
_exptl_absorpt_coefficient_mu    39.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.27273
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
'CrysAlisPro, Agilent Technologies,Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7737
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_sigmaI/netI    0.0511
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.35
_diffrn_reflns_theta_max         73.46
_reflns_number_total             3904
_reflns_number_gt                3342
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'CrysAlisPro, Agilent Technologies,Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)'
_computing_cell_refinement       
'CrysAlisPro, Agilent Technologies,Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)'
_computing_data_reduction        
'CrysAlisPro, Agilent Technologies,Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL

_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)+(0.0717P)²+0.0000P] 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         3904
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0424
_refine_ls_wR_factor_ref         0.1167
_refine_ls_wR_factor_gt          0.1094
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.002
_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
Hg1 Hg 0.591053(12) 0.70141(3) 0.90520(2) 0.01869(13) Uani 1 1 d . . .
I1 I 0.52949(2) 0.90005(5) 0.90400(4) 0.02058(15) Uani 1 1 d . . .
I2 I 0.67576(2) 0.61182(6) 0.99057(4) 0.02838(17) Uani 1 1 d . . .
S2 S 0.42907(8) 0.18273(19) 0.82321(14) 0.0201(4) Uani 1 1 d . . .
S1 S 0.31757(8) 0.2278(2) 0.53102(14) 0.0216(4) Uani 1 1 d . . .
N2 N 0.5327(2) 0.5219(7) 0.8931(4) 0.0164(14) Uani 1 1 d . . .
N1 N 0.3796(3) 0.2810(7) 0.2498(4) 0.0180(14) Uani 1 1 d . . .
C14 C 0.4659(3) 0.3171(8) 0.8501(5) 0.0151(16) Uani 1 1 d . . .
C12 C 0.3847(3) 0.1738(9) 0.3971(5) 0.0193(17) Uani 1 1 d . . .
H12 H 0.4017 0.1134 0.4376 0.023 Uiso 1 1 calc R . .
C8 C 0.3437(3) 0.2436(8) 0.4248(5) 0.0173(16) Uani 1 1 d . . .
C10 C 0.3405(3) 0.3468(9) 0.2763(6) 0.0215(17) Uani 1 1 d . . .
H10 H 0.3249 0.4073 0.2342 0.026 Uiso 1 1 calc R . .
C6 C 0.3335(3) 0.1319(8) 0.7571(5) 0.0156(15) Uani 1 1 d . . .
C11 C 0.4002(3) 0.1947(8) 0.3094(5) 0.0178(16) Uani 1 1 d . . .
H11 H 0.4273 0.1444 0.2902 0.021 Uiso 1 1 calc R . .
C15 C 0.4502(3) 0.4446(8) 0.8372(6) 0.0196(17) Uani 1 1 d . . .
H5 H 0.4164 0.4638 0.8147 0.023 Uiso 1 1 calc R . .
C16 C 0.4847(3) 0.5417(8) 0.8575(6) 0.0181(16) Uani 1 1 d . . .
H6 H 0.4740 0.6271 0.8458 0.022 Uiso 1 1 calc R . .
C4 C 0.2961(3) -0.0411(8) 0.6647(6) 0.0223(18) Uani 1 1 d . . .
H4 H 0.2927 -0.0877 0.6082 0.027 Uiso 1 1 calc R . .
C9 C 0.3211(3) 0.3326(8) 0.3616(6) 0.0192(17) Uani 1 1 d . . .
H9 H 0.2929 0.3821 0.3773 0.023 Uiso 1 1 calc R . .
C18 C 0.5469(3) 0.4016(8) 0.9096(5) 0.0180(17) Uani 1 1 d . . .
H8 H 0.5803 0.3861 0.9359 0.022 Uiso 1 1 calc R . .
C7 C 0.3549(3) 0.1019(8) 0.5900(6) 0.0190(17) Uani 1 1 d . . .
C13 C 0.3688(3) 0.2440(8) 0.7729(5) 0.0171(16) Uani 1 1 d . . .
C3 C 0.2689(3) -0.0792(9) 0.7386(7) 0.027(2) Uani 1 1 d . . .
H3 H 0.2469 -0.1509 0.7322 0.032 Uiso 1 1 calc R . .
C5 C 0.3281(3) 0.0640(8) 0.6729(5) 0.0176(16) Uani 1 1 d . . .
C2 C 0.2740(3) -0.0125(10) 0.8207(6) 0.028(2) Uani 1 1 d . . .
H2 H 0.2557 -0.0392 0.8711 0.034 Uiso 1 1 calc R . .
C17 C 0.5156(3) 0.2983(8) 0.8905(5) 0.0183(16) Uani 1 1 d . . .
H7 H 0.5274 0.2144 0.9045 0.022 Uiso 1 1 calc R . .
C1 C 0.3054(3) 0.0930(9) 0.8308(6) 0.025(2) Uani 1 1 d . . .
H1 H 0.3080 0.1392 0.8875 0.030 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
Hg1 N2 2.432(7) . ?
Hg1 N1 2.441(7) 5_666 ?
Hg1 I1 2.6433(6) . ?
Hg1 I2 2.6454(7) . ?
S2 C14 1.738(9) . ?
S2 C13 1.817(8) . ?
S1 C8 1.745(8) . ?
S1 C7 1.819(8) . ?
N2 C18 1.331(11) . ?
N2 C16 1.349(10) . ?
N1 C10 1.327(12) . ?
N1 C11 1.335(11) . ?
N1 Hg1 2.441(7) 5_666 ?
C14 C15 1.407(12) . ?
C14 C17 1.410(11) . ?
C12 C11 1.384(11) . ?
C12 C8 1.396(12) . ?
C8 C9 1.406(12) . ?
C10 C9 1.385(12) . ?
C6 C5 1.409(12) . ?
C6 C1 1.411(12) . ?
C6 C13 1.507(11) . ?
C15 C16 1.382(12) . ?
C4 C5 1.389(12) . ?
C4 C3 1.396(13) . ?
C18 C17 1.378(12) . ?
C7 C5 1.495(11) . ?
C3 C2 1.376(15) . ?
C2 C1 1.384(14) . ?

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
N2 Hg1 N1 103.9(2) . 5_666 ?
N2 Hg1 I1 102.70(16) . . ?
N1 Hg1 I1 100.18(17) 5_666 . ?
N2 Hg1 I2 105.65(15) . . ?
N1 Hg1 I2 97.76(17) 5_666 . ?
I1 Hg1 I2 141.47(2) . . ?
C14 S2 C13 105.2(4) . . ?
C8 S1 C7 104.1(4) . . ?
C18 N2 C16 117.2(7) . . ?
C18 N2 Hg1 123.4(5) . . ?
C16 N2 Hg1 118.9(6) . . ?
C10 N1 C11 117.0(7) . . ?
C10 N1 Hg1 122.7(5) . 5_666 ?
C11 N1 Hg1 120.1(6) . 5_666 ?
C15 C14 C17 116.3(8) . . ?
C15 C14 S2 125.8(6) . . ?
C17 C14 S2 117.9(6) . . ?
C11 C12 C8 118.4(8) . . ?
C12 C8 C9 117.6(7) . . ?
C12 C8 S1 125.3(6) . . ?
C9 C8 S1 117.2(6) . . ?
N1 C10 C9 123.9(8) . . ?
C5 C6 C1 119.1(8) . . ?
C5 C6 C13 122.9(7) . . ?
C1 C6 C13 118.0(8) . . ?
N1 C11 C12 124.4(8) . . ?
C16 C15 C14 119.2(8) . . ?
N2 C16 C15 123.7(8) . . ?
C5 C4 C3 120.8(8) . . ?
C10 C9 C8 118.8(8) . . ?
N2 C18 C17 123.4(7) . . ?
C5 C7 S1 107.1(6) . . ?
C6 C13 S2 107.4(6) . . ?
C2 C3 C4 119.7(9) . . ?
C4 C5 C6 119.5(8) . . ?
C4 C5 C7 117.9(8) . . ?
C6 C5 C7 122.6(8) . . ?
C3 C2 C1 120.9(8) . . ?
C18 C17 C14 120.0(8) . . ?
C2 C1 C6 120.0(9) . . ?

_diffrn_measured_fraction_theta_max 0.970
_diffrn_reflns_theta_full        73.46
_diffrn_measured_fraction_theta_full 0.970
_refine_diff_density_max         3.055
_refine_diff_density_min         -1.867
_refine_diff_density_rms         0.281
