# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_05gs06
_database_code_depnum_ccdc_archive 'CCDC 1452050'
_audit_update_record             
;
2016-02-06 deposited with the CCDC.
2016-04-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H8 N4 S'
_chemical_formula_sum            'C8 H8 N4 S'
_chemical_formula_weight         192.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
S S 0.3331 0.5567 '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'
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'

_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                   11.447(4)
_cell_length_b                   5.0219(9)
_cell_length_c                   15.967(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.41(2)
_cell_angle_gamma                90
_cell_volume                     917.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      21.32
_cell_measurement_theta_max      46.99

_exptl_crystal_description       needle
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_F_000             400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.620
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    2.784
_shelx_estimated_absorpt_T_min   0.277
_shelx_estimated_absorpt_T_max   0.731
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.379
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   '(North, Phillips & Mathews, 1968)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Enraf Nonius, MACH3'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            1967
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_av_R_equivalents  0.0108
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.863
_diffrn_reflns_theta_max         75.049
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1890
_reflns_number_gt                1353
_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       'CAD4-Express Software (Nonius, 1997)'
_computing_cell_refinement       'CAD4-Express Software (Nonius, 1997)'
_computing_data_reduction        'GENHKL (Kretchmar, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'PLATON (Spek, 2004)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_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)+(0.1167P)²+0.0864P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1890
_refine_ls_number_parameters     121
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0878
_refine_ls_R_factor_gt           0.0581
_refine_ls_wR_factor_ref         0.1751
_refine_ls_wR_factor_gt          0.1533
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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 0.19838(7) -0.05011(17) 0.53621(5) 0.0574(3) Uani 1 1 d . . . . .
N11 N 0.3501(2) 0.7220(6) 0.30338(19) 0.0625(7) Uani 1 1 d . . . . .
N12 N 0.0767(2) 0.4519(6) 0.36981(17) 0.0560(6) Uani 1 1 d . . . . .
N13 N 0.0681(2) 0.2564(6) 0.42923(16) 0.0569(6) Uani 1 1 d . . . . .
H13A H -0.008(3) 0.178(7) 0.438(2) 0.068 Uiso 1 1 d . U . . .
N14 N 0.25208(18) 0.3387(5) 0.42218(13) 0.0447(5) Uani 1 1 d . . . . .
C11 C 0.3889(3) 0.9046(7) 0.2490(2) 0.0694(10) Uani 1 1 d . . . . .
H11 H 0.4703 0.9095 0.2479 0.083 Uiso 1 1 d R U . . .
C12 C 0.3186(3) 1.0641(7) 0.2004(2) 0.0619(8) Uani 1 1 d . . . . .
H12 H 0.3542 1.2017 0.1601 0.074 Uiso 1 1 d R U . . .
C13 C 0.1992(3) 1.0371(7) 0.2071(2) 0.0609(8) Uani 1 1 d . . . . .
H13 H 0.1512 1.1319 0.1733 0.073 Uiso 1 1 d R U . . .
C14 C 0.1560(3) 0.8532(7) 0.26160(19) 0.0565(7) Uani 1 1 d . . . . .
H14 H 0.0697 0.8206 0.2613 0.068 Uiso 1 1 d R U . . .
C15 C 0.2344(2) 0.7000(6) 0.30910(17) 0.0460(6) Uani 1 1 d . . . . .
C16 C 0.1891(2) 0.4998(6) 0.36665(17) 0.0459(6) Uani 1 1 d . . . . .
C17 C 0.1711(2) 0.1825(6) 0.46274(17) 0.0486(6) Uani 1 1 d . . . . .
C18 C 0.3747(2) 0.3375(8) 0.4433(2) 0.0647(9) Uani 1 1 d . . . . .
H18A H 0.3902 0.4860 0.4719 0.097 Uiso 1 1 d R U . . .
H18B H 0.4191 0.3213 0.4003 0.097 Uiso 1 1 d R U . . .
H18C H 0.3949 0.1777 0.4822 0.097 Uiso 1 1 d 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 C17 1.679(3) . ?
N11 C15 1.334(3) . ?
N11 C11 1.346(4) . ?
N12 C16 1.312(3) . ?
N12 N13 1.370(3) . ?
N13 C17 1.336(4) . ?
N13 H13A 0.97(3) . ?
N14 C17 1.387(3) . ?
N14 C16 1.389(3) . ?
N14 C18 1.435(3) . ?
C11 C12 1.364(5) . ?
C11 H11 0.9319 . ?
C12 C13 1.380(4) . ?
C12 H12 1.0346 . ?
C13 C14 1.370(4) . ?
C13 H13 0.8971 . ?
C14 C15 1.393(4) . ?
C14 H14 1.0010 . ?
C15 C16 1.465(4) . ?
C18 H18A 0.8902 . ?
C18 H18B 0.8671 . ?
C18 H18C 1.0377 . ?

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
C15 N11 C11 116.4(3) . . ?
C16 N12 N13 104.2(2) . . ?
C17 N13 N12 113.5(2) . . ?
C17 N13 H13A 128(2) . . ?
N12 N13 H13A 118(2) . . ?
C17 N14 C16 106.6(2) . . ?
C17 N14 C18 123.3(2) . . ?
C16 N14 C18 129.9(2) . . ?
N11 C11 C12 124.5(3) . . ?
N11 C11 H11 112.1 . . ?
C12 C11 H11 123.3 . . ?
C11 C12 C13 118.0(3) . . ?
C11 C12 H12 120.7 . . ?
C13 C12 H12 121.3 . . ?
C14 C13 C12 119.3(3) . . ?
C14 C13 H13 120.9 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 118.7(3) . . ?
C13 C14 H14 118.6 . . ?
C15 C14 H14 122.4 . . ?
N11 C15 C14 123.0(3) . . ?
N11 C15 C16 117.8(3) . . ?
C14 C15 C16 119.1(2) . . ?
N12 C16 N14 111.3(2) . . ?
N12 C16 C15 120.9(2) . . ?
N14 C16 C15 127.9(2) . . ?
N13 C17 N14 104.4(2) . . ?
N13 C17 S1 128.3(2) . . ?
N14 C17 S1 127.2(2) . . ?
N14 C18 H18A 107.4 . . ?
N14 C18 H18B 113.8 . . ?
H18A C18 H18B 111.8 . . ?
N14 C18 H18C 110.2 . . ?
H18A C18 H18C 107.6 . . ?
H18B C18 H18C 105.9 . . ?

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
C16 N12 N13 C17 0.0(4) . . . . ?
C15 N11 C11 C12 -0.1(6) . . . . ?
N11 C11 C12 C13 -0.1(6) . . . . ?
C11 C12 C13 C14 0.0(5) . . . . ?
C12 C13 C14 C15 0.4(5) . . . . ?
C11 N11 C15 C14 0.6(5) . . . . ?
C11 N11 C15 C16 178.9(3) . . . . ?
C13 C14 C15 N11 -0.7(5) . . . . ?
C13 C14 C15 C16 -179.1(3) . . . . ?
N13 N12 C16 N14 0.4(3) . . . . ?
N13 N12 C16 C15 179.7(3) . . . . ?
C17 N14 C16 N12 -0.6(3) . . . . ?
C18 N14 C16 N12 -175.1(3) . . . . ?
C17 N14 C16 C15 -179.9(3) . . . . ?
C18 N14 C16 C15 5.6(5) . . . . ?
N11 C15 C16 N12 -174.0(3) . . . . ?
C14 C15 C16 N12 4.5(4) . . . . ?
N11 C15 C16 N14 5.3(4) . . . . ?
C14 C15 C16 N14 -176.2(3) . . . . ?
N12 N13 C17 N14 -0.4(3) . . . . ?
N12 N13 C17 S1 -179.4(2) . . . . ?
C16 N14 C17 N13 0.6(3) . . . . ?
C18 N14 C17 N13 175.5(3) . . . . ?
C16 N14 C17 S1 179.6(2) . . . . ?
C18 N14 C17 S1 -5.4(4) . . . . ?

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
N13 H13A S1 0.97(3) 2.32(3) 3.281(3) 172(3) 3_556
C18 H18C S1 1.04 2.69 3.196(3) 110.2 .

_refine_diff_density_max         0.409
_refine_diff_density_min         -0.523
_refine_diff_density_rms         0.081
####################################################################### 
# 
# 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_05rr01
_database_code_depnum_ccdc_archive 'CCDC 1452051'
_audit_update_record             
;
2016-02-06 deposited with the CCDC.
2016-04-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H7 N5 S'
_chemical_formula_sum            'C7 H7 N5 S'
_chemical_formula_weight         193.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
S S 0.1246 0.1234 '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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   5.6677(12)
_cell_length_b                   14.228(3)
_cell_length_c                   10.921(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.939(4)
_cell_angle_gamma                90
_cell_volume                     864.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1011
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      26.905

_exptl_crystal_description       prism
_exptl_crystal_colour            Brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_F_000             400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.331
_shelx_estimated_absorpt_T_min   0.839
_shelx_estimated_absorpt_T_max   0.934
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.898
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker, SMART CCD-1000'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8146
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.378
_diffrn_reflns_theta_max         27.473
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1977
_reflns_number_gt                1539
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 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       'SMART Software (Bruker, 1997)'
_computing_cell_refinement       'SMART Software (Bruker, 1997)'
_computing_data_reduction        'SAINT Software (Bruker, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'PLATON (Spek, 2004)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_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)+(0.0606P)²+0.2017P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1977
_refine_ls_number_parameters     121
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0395
_refine_ls_wR_factor_ref         0.1126
_refine_ls_wR_factor_gt          0.1045
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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 1.54326(8) 0.56994(3) 0.19407(5) 0.04711(18) Uani 1 1 d . . . . .
N11 N 0.8406(3) 0.34342(11) 0.35964(14) 0.0466(4) Uani 1 1 d . . . . .
N12 N 1.0555(3) 0.38173(10) 0.07446(14) 0.0403(4) Uani 1 1 d . . . . .
N13 N 1.2395(3) 0.44142(11) 0.06473(15) 0.0412(4) Uani 1 1 d . . . . .
H13A H 1.296(4) 0.4417(15) -0.001(2) 0.049 Uiso 1 1 d . U . . .
N14 N 1.1772(2) 0.46110(10) 0.24952(13) 0.0364(3) Uani 1 1 d . . . . .
N16 N 0.4970(3) 0.24132(13) 0.19514(15) 0.0493(4) Uani 1 1 d . . . . .
C11 C 0.6711(4) 0.29265(14) 0.39809(18) 0.0496(5) Uani 1 1 d . . . . .
H11 H 0.6683 0.2905 0.4829 0.060 Uiso 1 1 d R U . . .
C12 C 0.4996(3) 0.24314(14) 0.31688(18) 0.0468(5) Uani 1 1 d . . . . .
H12 H 0.3825 0.2101 0.3483 0.056 Uiso 1 1 d R U . . .
C14 C 0.6677(3) 0.29008(13) 0.15599(17) 0.0443(4) Uani 1 1 d . . . . .
H14 H 0.6739 0.2897 0.0715 0.053 Uiso 1 1 d R U . . .
C15 C 0.8374(3) 0.34176(11) 0.23716(15) 0.0350(4) Uani 1 1 d . . . . .
C16 C 1.0204(3) 0.39519(12) 0.18783(15) 0.0345(4) Uani 1 1 d . . . . .
C17 C 1.3192(3) 0.49065(12) 0.16831(16) 0.0366(4) Uani 1 1 d . . . . .
C18 C 1.1918(4) 0.50026(15) 0.37425(18) 0.0536(5) Uani 1 1 d . . . . .
H18A H 1.0381 0.5254 0.3821 0.080 Uiso 1 1 d R U . . .
H18B H 1.3098 0.5495 0.3875 0.080 Uiso 1 1 d R U . . .
H18C H 1.2370 0.4517 0.4353 0.080 Uiso 1 1 d 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 C17 1.6819(18) . ?
N11 C11 1.332(2) . ?
N11 C15 1.334(2) . ?
N12 C16 1.305(2) . ?
N12 N13 1.365(2) . ?
N13 C17 1.334(2) . ?
N13 H13A 0.84(2) . ?
N14 C17 1.372(2) . ?
N14 C16 1.377(2) . ?
N14 C18 1.460(2) . ?
N16 C14 1.325(2) . ?
N16 C12 1.327(2) . ?
C11 C12 1.379(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C14 C15 1.389(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.468(2) . ?
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
C11 N11 C15 115.65(16) . . ?
C16 N12 N13 103.82(14) . . ?
C17 N13 N12 113.67(15) . . ?
C17 N13 H13A 126.8(15) . . ?
N12 N13 H13A 119.4(15) . . ?
C17 N14 C16 107.21(14) . . ?
C17 N14 C18 123.37(15) . . ?
C16 N14 C18 129.33(14) . . ?
C14 N16 C12 116.30(16) . . ?
N11 C11 C12 122.48(18) . . ?
N11 C11 H11 118.8 . . ?
C12 C11 H11 118.8 . . ?
N16 C12 C11 121.80(18) . . ?
N16 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
N16 C14 C15 122.06(17) . . ?
N16 C14 H14 119.0 . . ?
C15 C14 H14 119.0 . . ?
N11 C15 C14 121.69(16) . . ?
N11 C15 C16 118.84(15) . . ?
C14 C15 C16 119.47(15) . . ?
N12 C16 N14 111.33(14) . . ?
N12 C16 C15 121.18(15) . . ?
N14 C16 C15 127.47(15) . . ?
N13 C17 N14 103.96(15) . . ?
N13 C17 S1 128.13(14) . . ?
N14 C17 S1 127.91(14) . . ?
N14 C18 H18A 109.5 . . ?
N14 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N14 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
C16 N12 N13 C17 0.3(2) . . . . ?
C15 N11 C11 C12 -1.4(3) . . . . ?
C14 N16 C12 C11 -0.3(3) . . . . ?
N11 C11 C12 N16 1.7(3) . . . . ?
C12 N16 C14 C15 -1.2(3) . . . . ?
C11 N11 C15 C14 -0.1(3) . . . . ?
C11 N11 C15 C16 -179.34(16) . . . . ?
N16 C14 C15 N11 1.4(3) . . . . ?
N16 C14 C15 C16 -179.31(17) . . . . ?
N13 N12 C16 N14 -0.26(19) . . . . ?
N13 N12 C16 C15 -178.63(15) . . . . ?
C17 N14 C16 N12 0.13(19) . . . . ?
C18 N14 C16 N12 176.53(18) . . . . ?
C17 N14 C16 C15 178.37(16) . . . . ?
C18 N14 C16 C15 -5.2(3) . . . . ?
N11 C15 C16 N12 166.39(16) . . . . ?
C14 C15 C16 N12 -12.9(2) . . . . ?
N11 C15 C16 N14 -11.7(3) . . . . ?
C14 C15 C16 N14 169.02(17) . . . . ?
N12 N13 C17 N14 -0.2(2) . . . . ?
N12 N13 C17 S1 179.31(13) . . . . ?
C16 N14 C17 N13 0.07(18) . . . . ?
C18 N14 C17 N13 -176.60(17) . . . . ?
C16 N14 C17 S1 -179.48(13) . . . . ?
C18 N14 C17 S1 3.8(3) . . . . ?

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
N13 H13A S1 0.84(2) 2.46(2) 3.2941(17) 176(2) 3_865
C11 H11 N16 0.93 2.72 3.449(3) 135.7 4_666
C12 H12 S1 0.93 3.10 3.926(2) 149.4 2_645

_refine_diff_density_max         0.219
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.066
####################################################################### 
# 
# 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_00gs25
_database_code_depnum_ccdc_archive 'CCDC 1452052'
_audit_update_record             
;
2016-02-06 deposited with the CCDC.
2016-04-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H14 Hg N8 S2'
_chemical_formula_sum            'C16 H14 Hg N8 S2'
_chemical_formula_weight         583.06

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Hg Hg -2.3894 9.2266 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_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                   21.6688(14)
_cell_length_b                   11.3368(17)
_cell_length_c                   8.2128(5)
_cell_angle_alpha                90
_cell_angle_beta                 107.851(6)
_cell_angle_gamma                90
_cell_volume                     1920.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      10.11
_cell_measurement_theta_max      20.93

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.017
_exptl_crystal_F_000             1112
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    8.251
_shelx_estimated_absorpt_T_min   0.110
_shelx_estimated_absorpt_T_max   0.438
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.737
_exptl_absorpt_correction_T_max  0.915
_exptl_absorpt_process_details   '(North et al., 1968)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CAD4 Enraf Nonius'
_diffrn_measurement_method       omega/2theta
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2965
_diffrn_reflns_av_unetI/netI     0.0732
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_theta_min         3.069
_diffrn_reflns_theta_max         29.972
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2784
_reflns_number_gt                1850
_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       'CAD4-Express Software (Nonius, 1994)'
_computing_cell_refinement       'CAD4-Express Software (Nonius, 1994)'
_computing_data_reduction        'GENHKL (Kretschmar, 1997)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_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)+(0.0469P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2784
_refine_ls_number_parameters     124
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0973
_refine_ls_R_factor_gt           0.0366
_refine_ls_wR_factor_ref         0.0929
_refine_ls_wR_factor_gt          0.0804
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_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
Hg1 Hg 0.0000 0.06684(3) -0.2500 0.04651(13) Uani 1 2 d S T P . .
S1 S 0.02106(7) 0.18785(15) 0.01405(19) 0.0553(4) Uani 1 1 d . . . . .
N1 N 0.2912(2) 0.1921(5) 0.3386(7) 0.0542(12) Uani 1 1 d . . . . .
N2 N 0.1535(2) 0.0198(4) 0.3608(6) 0.0440(11) Uani 1 1 d . . . . .
N3 N 0.0907(2) 0.0395(4) 0.2593(6) 0.0450(12) Uani 1 1 d . . . . .
N4 N 0.1516(2) 0.1641(4) 0.1795(5) 0.0374(9) Uani 1 1 d . . . . .
C1 C 0.3545(3) 0.2047(7) 0.4242(9) 0.0625(17) Uani 1 1 d . . . . .
H1 H 0.3768 0.2647 0.3892 0.075 Uiso 1 1 calc R U . . .
C2 C 0.3882(3) 0.1369(6) 0.5570(9) 0.0591(17) Uani 1 1 d . . . . .
H2 H 0.4324 0.1486 0.6091 0.071 Uiso 1 1 calc R U . . .
C3 C 0.3549(3) 0.0494(6) 0.6128(9) 0.0588(17) Uani 1 1 d . . . . .
H3 H 0.3761 0.0015 0.7049 0.071 Uiso 1 1 calc R U . . .
C4 C 0.2894(3) 0.0344(6) 0.5295(8) 0.0497(14) Uani 1 1 d . . . . .
H4 H 0.2661 -0.0244 0.5634 0.060 Uiso 1 1 calc R U . . .
C5 C 0.2595(2) 0.1082(5) 0.3953(7) 0.0376(12) Uani 1 1 d . . . . .
C6 C 0.1890(2) 0.0966(5) 0.3091(7) 0.0376(12) Uani 1 1 d . . . . .
C7 C 0.0900(2) 0.1262(5) 0.1516(7) 0.0412(12) Uani 1 1 d . . . . .
C8 C 0.1705(3) 0.2532(5) 0.0755(8) 0.0523(15) Uani 1 1 d . . . . .
H8A H 0.2011 0.3066 0.1487 0.078 Uiso 1 1 calc R U . . .
H8B H 0.1328 0.2963 0.0107 0.078 Uiso 1 1 calc R U . . .
H8C H 0.1900 0.2155 -0.0012 0.078 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
Hg1 N3 2.286(4) 5 y
Hg1 N3 2.286(4) 6 y
Hg1 S1 2.4872(15) . y
Hg1 S1 2.4872(15) 2_554 y
Hg1 Hg1 4.3772(4) 5 y
S1 C7 1.720(5) . ?
S1 S1 4.347(4) 5 y
N1 C5 1.338(7) . ?
N1 C1 1.343(7) . ?
N2 C6 1.314(7) . ?
N2 N3 1.379(6) . ?
N3 C7 1.320(8) . ?
N3 Hg1 2.286(4) 5 ?
N4 C6 1.359(7) . ?
N4 C7 1.354(6) . ?
N4 C8 1.460(7) . ?
C1 C2 1.351(10) . ?
C1 H1 0.9300 . ?
C2 C3 1.386(10) . ?
C2 H2 0.9300 . ?
C3 C4 1.383(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(9) . ?
C4 H4 0.9300 . ?
C5 C6 1.480(7) . ?
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
N3 Hg1 N3 116.4(2) 5 6 y
N3 Hg1 S1 104.24(13) 5 . y
N3 Hg1 S1 109.60(12) 6 . y
N3 Hg1 S1 109.60(12) 5 2_554 y
N3 Hg1 S1 104.24(13) 6 2_554 y
S1 Hg1 S1 113.05(8) . 2_554 y
N3 Hg1 Hg1 66.53(12) 5 5 ?
N3 Hg1 Hg1 91.90(12) 6 5 ?
S1 Hg1 Hg1 54.95(4) . 5 ?
S1 Hg1 Hg1 162.98(4) 2_554 5 ?
C7 S1 Hg1 103.82(19) . . ?
C7 S1 S1 76.3(2) . 5 ?
Hg1 S1 S1 55.52(4) . 5 ?
C5 N1 C1 116.4(5) . . ?
C6 N2 N3 105.3(4) . . ?
C7 N3 N2 109.4(4) . . ?
C7 N3 Hg1 122.5(3) . 5 ?
N2 N3 Hg1 127.9(4) . 5 ?
C6 N4 C7 105.9(4) . . ?
C6 N4 C8 129.9(4) . . ?
C7 N4 C8 124.0(5) . . ?
N1 C1 C2 125.1(6) . . ?
N1 C1 H1 117.4 . . ?
C2 C1 H1 117.4 . . ?
C1 C2 C3 117.8(6) . . ?
C1 C2 H2 121.1 . . ?
C3 C2 H2 121.1 . . ?
C4 C3 C2 119.0(6) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C5 C4 C3 118.8(6) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
N1 C5 C4 123.0(5) . . ?
N1 C5 C6 117.5(5) . . ?
C4 C5 C6 119.5(5) . . ?
N2 C6 N4 111.0(4) . . ?
N2 C6 C5 121.6(5) . . ?
N4 C6 C5 127.2(5) . . ?
N3 C7 N4 108.4(4) . . ?
N3 C7 S1 124.9(4) . . ?
N4 C7 S1 126.5(5) . . ?
N4 C8 H8A 109.5 . . ?
N4 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N4 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 N2 N3 C7 -0.2(6) . . . . ?
C6 N2 N3 Hg1 174.2(4) . . . 5 ?
C5 N1 C1 C2 2.5(10) . . . . ?
N1 C1 C2 C3 -1.8(11) . . . . ?
C1 C2 C3 C4 0.9(10) . . . . ?
C2 C3 C4 C5 -0.9(10) . . . . ?
C1 N1 C5 C4 -2.4(9) . . . . ?
C1 N1 C5 C6 176.9(5) . . . . ?
C3 C4 C5 N1 1.8(9) . . . . ?
C3 C4 C5 C6 -177.6(5) . . . . ?
N3 N2 C6 N4 0.0(6) . . . . ?
N3 N2 C6 C5 176.1(5) . . . . ?
C7 N4 C6 N2 0.2(6) . . . . ?
C8 N4 C6 N2 -174.8(5) . . . . ?
C7 N4 C6 C5 -175.6(5) . . . . ?
C8 N4 C6 C5 9.3(9) . . . . ?
N1 C5 C6 N2 -177.2(5) . . . . ?
C4 C5 C6 N2 2.2(8) . . . . ?
N1 C5 C6 N4 -1.8(8) . . . . ?
C4 C5 C6 N4 177.6(5) . . . . ?
N2 N3 C7 N4 0.3(6) . . . . ?
Hg1 N3 C7 N4 -174.5(3) 5 . . . ?
N2 N3 C7 S1 -174.3(4) . . . . ?
Hg1 N3 C7 S1 10.9(7) 5 . . . ?
C6 N4 C7 N3 -0.3(6) . . . . ?
C8 N4 C7 N3 175.1(5) . . . . ?
C6 N4 C7 S1 174.2(4) . . . . ?
C8 N4 C7 S1 -10.4(8) . . . . ?
Hg1 S1 C7 N3 -89.8(5) . . . . ?
S1 S1 C7 N3 -41.2(5) 5 . . . ?
Hg1 S1 C7 N4 96.5(5) . . . . ?
S1 S1 C7 N4 145.2(5) 5 . . . ?

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
C1 H1 S1 0.93 3.02 3.664(6) 127.4 8_556
C2 H2 S1 0.93 2.94 3.602(6) 129.1 8_556
C8 H8B S1 0.96 2.72 3.207(6) 111.8 .

_refine_diff_density_max         1.299
_refine_diff_density_min         -1.801
_refine_diff_density_rms         0.178
####################################################################### 
# 
# 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_99gs07
_database_code_depnum_ccdc_archive 'CCDC 1452053'
_audit_update_record             
;
2016-02-06 deposited with the CCDC.
2016-04-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H16 Br2 Hg N8 S2, H2 O'
_chemical_formula_sum            'C16 H20 Br2 Hg N8 O S2'
_chemical_formula_weight         762.91

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Hg Hg -2.3894 9.2266 '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'
S S 0.1246 0.1234 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_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                   7.7077(6)
_cell_length_b                   16.2385(14)
_cell_length_c                   18.9449(14)
_cell_angle_alpha                80.783(9)
_cell_angle_beta                 86.817(9)
_cell_angle_gamma                86.277(8)
_cell_volume                     2333.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9.702
_cell_measurement_theta_max      17.121

_exptl_crystal_description       prism
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.172
_exptl_crystal_F_000             1440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    10.226
_shelx_estimated_absorpt_T_min   0.184
_shelx_estimated_absorpt_T_max   0.428
_exptl_absorpt_correction_type   Psi-scan
_exptl_absorpt_correction_T_min  0.720
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   '(North et al., 1968)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'MACH3 Nonius'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12049
_diffrn_reflns_av_unetI/netI     0.2965
_diffrn_reflns_av_R_equivalents  0.0913
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.346
_diffrn_reflns_theta_max         27.976
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             11230
_reflns_number_gt                4520
_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       'CAD4-Express Software (Nonius, 1994)'
_computing_cell_refinement       'CAD4-Express Software (Nonius, 1994)'
_computing_data_reduction        'GENHKL (Kretschmar, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          
;
 The H atoms of two water molecules, O(1) and O(2), were not located.

 In the formula are included the hydrogen atoms nonlocalized.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1231P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         11230
_refine_ls_number_parameters     541
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2689
_refine_ls_R_factor_gt           0.0675
_refine_ls_wR_factor_ref         0.2457
_refine_ls_wR_factor_gt          0.1742
_refine_ls_goodness_of_fit_ref   0.962
_refine_ls_restrained_S_all      0.962
_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
Hg1 Hg 0.81263(12) 0.10478(5) 0.25607(4) 0.0444(2) Uani 1 1 d . . . . .
Br11 Br 0.5433(3) -0.00201(12) 0.28395(11) 0.0491(5) Uani 1 1 d . . . . .
Br12 Br 0.9216(3) 0.07607(14) 0.13236(11) 0.0578(6) Uani 1 1 d . . . . .
S11 S 0.6698(7) 0.2505(3) 0.2382(2) 0.0393(11) Uani 1 1 d . . . . .
S12 S 0.9711(8) 0.0740(3) 0.3684(3) 0.0513(14) Uani 1 1 d . . . . .
N11 N 0.609(2) 0.2229(9) 0.5449(8) 0.045(4) Uani 1 1 d . . . . .
N12 N 0.789(2) 0.3581(10) 0.3963(8) 0.046(4) Uani 1 1 d . . . . .
N13 N 0.803(2) 0.3451(10) 0.3269(9) 0.046(4) Uani 1 1 d . . . . .
H13 H 0.8666 0.3723 0.2935 0.056 Uiso 1 1 d R U . . .
N14 N 0.635(2) 0.2511(8) 0.3844(8) 0.034(4) Uani 1 1 d . . . . .
N21 N 0.947(3) -0.2675(10) 0.3392(9) 0.059(5) Uani 1 1 d . . . . .
N22 N 0.809(2) -0.1358(9) 0.4688(9) 0.048(4) Uani 1 1 d . . . . .
N23 N 0.826(2) -0.0528(9) 0.4580(8) 0.047(5) Uani 1 1 d . . . . .
H23 H 0.7854 -0.0206 0.4875 0.057 Uiso 1 1 d R U . . .
N24 N 0.959(2) -0.0949(9) 0.3690(8) 0.042(4) Uani 1 1 d . . . . .
C11 C 0.556(3) 0.2231(14) 0.6131(11) 0.061(7) Uani 1 1 d . . . . .
H11 H 0.5304 0.1722 0.6406 0.074 Uiso 1 1 d R U . . .
C12 C 0.536(4) 0.2912(15) 0.6449(12) 0.077(8) Uani 1 1 d . . . . .
H12 H 0.5000 0.2864 0.6930 0.092 Uiso 1 1 d R U . . .
C13 C 0.569(4) 0.3690(15) 0.6058(13) 0.078(9) Uani 1 1 d . . . . .
H13A H 0.5541 0.4177 0.6260 0.094 Uiso 1 1 d R U . . .
C14 C 0.626(3) 0.3699(13) 0.5347(13) 0.063(7) Uani 1 1 d . . . . .
H14 H 0.6576 0.4198 0.5071 0.076 Uiso 1 1 d R U . . .
C15 C 0.635(3) 0.2997(12) 0.5052(10) 0.044(5) Uani 1 1 d . . . . .
C16 C 0.696(3) 0.3002(11) 0.4313(10) 0.042(5) Uani 1 1 d . . . . .
C17 C 0.703(3) 0.2835(11) 0.3186(9) 0.037(4) Uani 1 1 d . . . . .
C18 C 0.511(3) 0.1879(11) 0.3997(9) 0.040(5) Uani 1 1 d . . . . .
H18A H 0.4395 0.1903 0.3594 0.060 Uiso 1 1 d R U . . .
H18B H 0.4390 0.1972 0.4410 0.060 Uiso 1 1 d R U . . .
H18C H 0.5711 0.1339 0.4089 0.060 Uiso 1 1 d R U . . .
C21 C 0.963(4) -0.3486(14) 0.3340(13) 0.075(8) Uani 1 1 d . . . . .
H21 H 0.9973 -0.3635 0.2897 0.090 Uiso 1 1 d R U . . .
C22 C 0.932(4) -0.4136(12) 0.3920(11) 0.071(8) Uani 1 1 d . . . . .
H22 H 0.9384 -0.4692 0.3853 0.085 Uiso 1 1 d R U . . .
C23 C 0.891(3) -0.3925(12) 0.4573(13) 0.065(7) Uani 1 1 d . . . . .
H23A H 0.8685 -0.4341 0.4959 0.078 Uiso 1 1 d R U . . .
C24 C 0.883(4) -0.3106(13) 0.4674(12) 0.071(8) Uani 1 1 d . . . . .
H24 H 0.8610 -0.2960 0.5127 0.086 Uiso 1 1 d R U . . .
C25 C 0.909(3) -0.2496(11) 0.4071(10) 0.045(5) Uani 1 1 d . . . . .
C26 C 0.885(3) -0.1612(11) 0.4150(10) 0.039(5) Uani 1 1 d . . . . .
C27 C 0.911(3) -0.0260(12) 0.3984(9) 0.044(5) Uani 1 1 d . . . . .
C28 C 1.069(3) -0.0976(13) 0.3033(10) 0.052(6) Uani 1 1 d . . . . .
H28A H 0.9974 -0.0894 0.2627 0.078 Uiso 1 1 d R U . . .
H28B H 1.1322 -0.1509 0.3064 0.078 Uiso 1 1 d R U . . .
H28C H 1.1498 -0.0541 0.2981 0.078 Uiso 1 1 d R U . . .
Hg2 Hg 1.27689(11) 0.38377(4) 0.23843(4) 0.0424(2) Uani 1 1 d . . . . .
Br21 Br 0.9882(3) 0.49056(12) 0.20663(11) 0.0465(5) Uani 1 1 d . . . . .
Br22 Br 1.3306(3) 0.41644(13) 0.36235(11) 0.0559(6) Uani 1 1 d . . . . .
S21 S 1.1691(7) 0.2382(3) 0.2536(2) 0.0409(12) Uani 1 1 d . . . . .
S22 S 1.4674(7) 0.4178(3) 0.1293(3) 0.0455(13) Uani 1 1 d . . . . .
N31 N 1.180(2) 0.2766(9) -0.0525(7) 0.040(4) Uani 1 1 d . . . . .
N32 N 1.372(2) 0.1376(9) 0.0913(9) 0.044(4) Uani 1 1 d . . . . .
N33 N 1.349(2) 0.1485(10) 0.1628(8) 0.045(4) Uani 1 1 d . . . . .
H33 H 1.4031 0.1176 0.1967 0.054 Uiso 1 1 d R U . . .
N34 N 1.180(2) 0.2425(9) 0.1072(8) 0.039(4) Uani 1 1 d . . . . .
N41 N 1.364(2) 0.7600(10) 0.1633(9) 0.050(4) Uani 1 1 d . . . . .
N42 N 1.267(2) 0.6300(10) 0.0327(9) 0.052(5) Uani 1 1 d . . . . .
N43 N 1.302(2) 0.5449(8) 0.0438(8) 0.037(4) Uani 1 1 d . . . . .
H43 H 1.2718 0.5127 0.0153 0.045 Uiso 1 1 d R U . . .
N44 N 1.4090(19) 0.5863(8) 0.1325(7) 0.033(3) Uani 1 1 d . . . . .
C31 C 1.145(3) 0.2789(12) -0.1217(11) 0.049(5) Uani 1 1 d . . . . .
H31 H 1.1060 0.3299 -0.1472 0.059 Uiso 1 1 d R U . . .
C32 C 1.162(3) 0.2107(14) -0.1572(10) 0.051(6) Uani 1 1 d . . . . .
H32 H 1.1338 0.2150 -0.2048 0.061 Uiso 1 1 d R U . . .
C33 C 1.222(4) 0.1373(15) -0.1197(13) 0.074(8) Uani 1 1 d . . . . .
H33A H 1.2445 0.0913 -0.1431 0.089 Uiso 1 1 d R U . . .
C34 C 1.251(3) 0.1292(14) -0.0489(12) 0.058(6) Uani 1 1 d . . . . .
H34 H 1.2840 0.0780 -0.0221 0.069 Uiso 1 1 d R U . . .
C35 C 1.228(3) 0.2032(11) -0.0179(10) 0.045(5) Uani 1 1 d . . . . .
C36 C 1.264(2) 0.1943(10) 0.0609(10) 0.035(4) Uani 1 1 d . . . . .
C37 C 1.238(3) 0.2101(10) 0.1733(10) 0.043(5) Uani 1 1 d . . . . .
C38 C 1.035(3) 0.3066(10) 0.0957(9) 0.039(5) Uani 1 1 d . . . . .
H38A H 0.9517 0.2887 0.0663 0.059 Uiso 1 1 d R U . . .
H38B H 1.0791 0.3585 0.0723 0.059 Uiso 1 1 d R U . . .
H38C H 0.9796 0.3144 0.1410 0.059 Uiso 1 1 d R U . . .
C41 C 1.347(3) 0.8415(13) 0.1701(12) 0.055(6) Uani 1 1 d . . . . .
H41 H 1.3724 0.8556 0.2139 0.066 Uiso 1 1 d R U . . .
C42 C 1.298(3) 0.9038(14) 0.1187(14) 0.063(7) Uani 1 1 d . . . . .
H42 H 1.2898 0.9588 0.1274 0.076 Uiso 1 1 d R U . . .
C43 C 1.259(4) 0.8861(14) 0.0540(15) 0.075(8) Uani 1 1 d . . . . .
H43A H 1.2225 0.9283 0.0177 0.090 Uiso 1 1 d R U . . .
C44 C 1.275(3) 0.8028(12) 0.0433(13) 0.067(7) Uani 1 1 d . . . . .
H44 H 1.2555 0.7891 -0.0013 0.080 Uiso 1 1 d R U . . .
C45 C 1.320(3) 0.7416(11) 0.0983(11) 0.045(5) Uani 1 1 d . . . . .
C46 C 1.330(3) 0.6531(11) 0.0883(10) 0.041(5) Uani 1 1 d . . . . .
C47 C 1.387(3) 0.5175(11) 0.1025(10) 0.039(5) Uani 1 1 d . . . . .
C48 C 1.499(3) 0.5877(13) 0.1978(10) 0.057(6) Uani 1 1 d . . . . .
H48A H 1.4148 0.5880 0.2372 0.086 Uiso 1 1 d R U . . .
H48B H 1.5633 0.6371 0.1925 0.086 Uiso 1 1 d R U . . .
H48C H 1.5766 0.5391 0.2067 0.086 Uiso 1 1 d R U . . .
O1 O 1.191(2) 0.4518(8) -0.0480(7) 0.060(4) Uani 1 1 d . . . . .
O2 O 0.665(2) 0.0454(9) 0.5506(8) 0.070(5) 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 S12 2.478(5) . y
Hg1 S11 2.525(5) . y
Hg1 Br12 2.549(2) . y
Hg1 Br11 2.765(2) . y
S11 C17 1.732(18) . ?
S12 C27 1.717(19) . ?
N11 C11 1.33(3) . ?
N11 C15 1.37(2) . ?
N12 C16 1.29(2) . ?
N12 N13 1.36(2) . ?
N13 C17 1.34(2) . ?
N13 H13 0.8600 . ?
N14 C17 1.36(2) . ?
N14 C16 1.40(2) . ?
N14 C18 1.43(2) . ?
N21 C21 1.33(2) . ?
N21 C25 1.38(2) . ?
N22 C26 1.26(2) . ?
N22 N23 1.345(19) . ?
N23 C27 1.30(2) . ?
N23 H23 0.8600 . ?
N24 C27 1.35(2) . ?
N24 C26 1.40(2) . ?
N24 C28 1.47(2) . ?
C11 C12 1.34(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.39(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.39(3) . ?
C13 H13A 0.9300 . ?
C14 C15 1.34(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.45(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C21 C22 1.42(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.35(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.37(3) . ?
C23 H23A 0.9300 . ?
C24 C25 1.40(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.47(2) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
Hg2 S22 2.478(5) . y
Hg2 S21 2.524(5) . y
Hg2 Br22 2.549(2) . y
Hg2 Br21 2.763(2) . y
S21 C37 1.70(2) . ?
S22 C47 1.703(19) . ?
N31 C35 1.31(2) . ?
N31 C31 1.35(2) . ?
N32 C36 1.29(2) . ?
N32 N33 1.39(2) . ?
N33 C37 1.31(2) . ?
N33 H33 0.8600 . ?
N34 C37 1.37(2) . ?
N34 C36 1.37(2) . ?
N34 C38 1.48(2) . ?
N41 C41 1.35(2) . ?
N41 C45 1.38(3) . ?
N42 C46 1.30(2) . ?
N42 N43 1.38(2) . ?
N43 C47 1.32(2) . ?
N43 H43 0.8600 . ?
N44 C47 1.36(2) . ?
N44 C46 1.39(2) . ?
N44 C48 1.45(2) . ?
C31 C32 1.38(3) . ?
C31 H31 0.9300 . ?
C32 C33 1.35(3) . ?
C32 H32 0.9300 . ?
C33 C34 1.36(3) . ?
C33 H33A 0.9300 . ?
C34 C35 1.42(3) . ?
C34 H34 0.9300 . ?
C35 C36 1.51(3) . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C41 C42 1.34(3) . ?
C41 H41 0.9300 . ?
C42 C43 1.36(3) . ?
C42 H42 0.9300 . ?
C43 C44 1.40(3) . ?
C43 H43A 0.9300 . ?
C44 C45 1.36(3) . ?
C44 H44 0.9300 . ?
C45 C46 1.48(2) . ?
C48 H48A 0.9600 . ?
C48 H48B 0.9600 . ?
C48 H48C 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
S12 Hg1 S11 112.02(16) . . y
S12 Hg1 Br12 127.26(16) . . y
S11 Hg1 Br12 106.30(12) . . y
S12 Hg1 Br11 102.29(14) . . y
S11 Hg1 Br11 105.72(13) . . y
Br12 Hg1 Br11 100.61(7) . . y
C17 S11 Hg1 102.1(6) . . ?
C27 S12 Hg1 99.9(6) . . ?
C11 N11 C15 115.8(17) . . ?
C16 N12 N13 107.0(16) . . ?
C17 N13 N12 109.5(15) . . ?
C17 N13 H13 125.2 . . ?
N12 N13 H13 125.2 . . ?
C17 N14 C16 104.9(15) . . ?
C17 N14 C18 126.7(16) . . ?
C16 N14 C18 128.0(15) . . ?
C21 N21 C25 115.3(17) . . ?
C26 N22 N23 105.1(15) . . ?
C27 N23 N22 113.4(16) . . ?
C27 N23 H23 123.3 . . ?
N22 N23 H23 123.3 . . ?
C27 N24 C26 105.5(15) . . ?
C27 N24 C28 125.9(16) . . ?
C26 N24 C28 128.7(16) . . ?
N11 C11 C12 125(2) . . ?
N11 C11 H11 117.6 . . ?
C12 C11 H11 117.6 . . ?
C11 C12 C13 120(2) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C12 C13 C14 116(2) . . ?
C12 C13 H13A 121.9 . . ?
C14 C13 H13A 121.9 . . ?
C15 C14 C13 121(2) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 N11 122.2(18) . . ?
C14 C15 C16 121.1(19) . . ?
N11 C15 C16 116.3(17) . . ?
N12 C16 N14 110.3(17) . . ?
N12 C16 C15 122.8(18) . . ?
N14 C16 C15 125.6(18) . . ?
N13 C17 N14 108.0(15) . . ?
N13 C17 S11 125.3(14) . . ?
N14 C17 S11 126.7(15) . . ?
N14 C18 H18A 109.5 . . ?
N14 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N14 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N21 C21 C22 124(2) . . ?
N21 C21 H21 118.1 . . ?
C22 C21 H21 118.1 . . ?
C23 C22 C21 118.3(19) . . ?
C23 C22 H22 120.9 . . ?
C21 C22 H22 120.9 . . ?
C22 C23 C24 121(2) . . ?
C22 C23 H23A 119.6 . . ?
C24 C23 H23A 119.6 . . ?
C23 C24 C25 118(2) . . ?
C23 C24 H24 121.2 . . ?
C25 C24 H24 121.2 . . ?
N21 C25 C24 123.8(18) . . ?
N21 C25 C26 117.1(16) . . ?
C24 C25 C26 118.9(18) . . ?
N22 C26 N24 110.6(16) . . ?
N22 C26 C25 123.7(17) . . ?
N24 C26 C25 125.3(17) . . ?
N23 C27 N24 105.3(16) . . ?
N23 C27 S12 127.2(16) . . ?
N24 C27 S12 127.2(15) . . ?
N24 C28 H28A 109.5 . . ?
N24 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
N24 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
S22 Hg2 S21 113.03(16) . . y
S22 Hg2 Br22 125.99(15) . . y
S21 Hg2 Br22 107.95(12) . . y
S22 Hg2 Br21 101.80(13) . . y
S21 Hg2 Br21 105.60(13) . . y
Br22 Hg2 Br21 99.38(7) . . y
C37 S21 Hg2 100.5(7) . . ?
C47 S22 Hg2 98.4(6) . . ?
C35 N31 C31 115.8(16) . . ?
C36 N32 N33 101.8(16) . . ?
C37 N33 N32 113.7(16) . . ?
C37 N33 H33 123.2 . . ?
N32 N33 H33 123.2 . . ?
C37 N34 C36 105.6(15) . . ?
C37 N34 C38 123.2(16) . . ?
C36 N34 C38 130.4(15) . . ?
C41 N41 C45 115.5(18) . . ?
C46 N42 N43 102.9(15) . . ?
C47 N43 N42 113.4(15) . . ?
C47 N43 H43 123.3 . . ?
N42 N43 H43 123.3 . . ?
C47 N44 C46 106.1(16) . . ?
C47 N44 C48 125.8(15) . . ?
C46 N44 C48 128.1(16) . . ?
N31 C31 C32 124.5(19) . . ?
N31 C31 H31 117.8 . . ?
C32 C31 H31 117.8 . . ?
C33 C32 C31 117(2) . . ?
C33 C32 H32 121.4 . . ?
C31 C32 H32 121.4 . . ?
C32 C33 C34 122(2) . . ?
C32 C33 H33A 119.2 . . ?
C34 C33 H33A 119.2 . . ?
C33 C34 C35 116(2) . . ?
C33 C34 H34 121.9 . . ?
C35 C34 H34 121.9 . . ?
N31 C35 C34 124.5(18) . . ?
N31 C35 C36 119.4(15) . . ?
C34 C35 C36 116.1(18) . . ?
N32 C36 N34 113.6(17) . . ?
N32 C36 C35 122.3(16) . . ?
N34 C36 C35 124.0(17) . . ?
N33 C37 N34 105.3(16) . . ?
N33 C37 S21 126.8(14) . . ?
N34 C37 S21 127.8(14) . . ?
N34 C38 H38A 109.5 . . ?
N34 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
N34 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C42 C41 N41 125(2) . . ?
C42 C41 H41 117.4 . . ?
N41 C41 H41 117.4 . . ?
C41 C42 C43 119(2) . . ?
C41 C42 H42 120.3 . . ?
C43 C42 H42 120.3 . . ?
C42 C43 C44 118(2) . . ?
C42 C43 H43A 120.9 . . ?
C44 C43 H43A 120.9 . . ?
C45 C44 C43 120(2) . . ?
C45 C44 H44 120.1 . . ?
C43 C44 H44 120.1 . . ?
C44 C45 N41 121.7(18) . . ?
C44 C45 C46 120(2) . . ?
N41 C45 C46 118.0(17) . . ?
N42 C46 N44 112.1(17) . . ?
N42 C46 C45 121.2(17) . . ?
N44 C46 C45 126.7(18) . . ?
N43 C47 N44 105.4(16) . . ?
N43 C47 S22 126.4(13) . . ?
N44 C47 S22 128.0(15) . . ?
N44 C48 H48A 109.5 . . ?
N44 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
N44 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 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
C16 N12 N13 C17 6(2) . . . . ?
C26 N22 N23 C27 0(2) . . . . ?
C15 N11 C11 C12 -4(4) . . . . ?
N11 C11 C12 C13 1(5) . . . . ?
C11 C12 C13 C14 -1(4) . . . . ?
C12 C13 C14 C15 5(4) . . . . ?
C13 C14 C15 N11 -8(4) . . . . ?
C13 C14 C15 C16 -179(2) . . . . ?
C11 N11 C15 C14 7(3) . . . . ?
C11 N11 C15 C16 179(2) . . . . ?
N13 N12 C16 N14 -4(2) . . . . ?
N13 N12 C16 C15 -172.1(18) . . . . ?
C17 N14 C16 N12 1(2) . . . . ?
C18 N14 C16 N12 -171.4(17) . . . . ?
C17 N14 C16 C15 168.5(19) . . . . ?
C18 N14 C16 C15 -4(3) . . . . ?
C14 C15 C16 N12 20(3) . . . . ?
N11 C15 C16 N12 -152(2) . . . . ?
C14 C15 C16 N14 -145(2) . . . . ?
N11 C15 C16 N14 42(3) . . . . ?
N12 N13 C17 N14 -5(2) . . . . ?
N12 N13 C17 S11 175.7(14) . . . . ?
C16 N14 C17 N13 3(2) . . . . ?
C18 N14 C17 N13 175.3(16) . . . . ?
C16 N14 C17 S11 -178.5(15) . . . . ?
C18 N14 C17 S11 -6(3) . . . . ?
Hg1 S11 C17 N13 113.7(17) . . . . ?
Hg1 S11 C17 N14 -65.1(17) . . . . ?
C25 N21 C21 C22 5(4) . . . . ?
N21 C21 C22 C23 -3(5) . . . . ?
C21 C22 C23 C24 -1(4) . . . . ?
C22 C23 C24 C25 3(4) . . . . ?
C21 N21 C25 C24 -2(4) . . . . ?
C21 N21 C25 C26 -178(2) . . . . ?
C23 C24 C25 N21 -2(4) . . . . ?
C23 C24 C25 C26 174(2) . . . . ?
N23 N22 C26 N24 2(2) . . . . ?
N23 N22 C26 C25 175.2(19) . . . . ?
C27 N24 C26 N22 -4(2) . . . . ?
C28 N24 C26 N22 175(2) . . . . ?
C27 N24 C26 C25 -176.4(19) . . . . ?
C28 N24 C26 C25 2(3) . . . . ?
N21 C25 C26 N22 162(2) . . . . ?
C24 C25 C26 N22 -15(3) . . . . ?
N21 C25 C26 N24 -26(3) . . . . ?
C24 C25 C26 N24 157(2) . . . . ?
N22 N23 C27 N24 -2(2) . . . . ?
N22 N23 C27 S12 -175.8(15) . . . . ?
C26 N24 C27 N23 3(2) . . . . ?
C28 N24 C27 N23 -175.2(18) . . . . ?
C26 N24 C27 S12 176.9(15) . . . . ?
C28 N24 C27 S12 -2(3) . . . . ?
Hg1 S12 C27 N23 -119.2(18) . . . . ?
Hg1 S12 C27 N24 68.6(18) . . . . ?
C36 N32 N33 C37 -2(2) . . . . ?
C46 N42 N43 C47 -2(2) . . . . ?
C35 N31 C31 C32 -2(3) . . . . ?
N31 C31 C32 C33 -1(3) . . . . ?
C31 C32 C33 C34 5(4) . . . . ?
C32 C33 C34 C35 -5(4) . . . . ?
C31 N31 C35 C34 2(3) . . . . ?
C31 N31 C35 C36 -177.8(18) . . . . ?
C33 C34 C35 N31 1(4) . . . . ?
C33 C34 C35 C36 -179(2) . . . . ?
N33 N32 C36 N34 3(2) . . . . ?
N33 N32 C36 C35 -174.7(16) . . . . ?
C37 N34 C36 N32 -3(2) . . . . ?
C38 N34 C36 N32 -172.3(17) . . . . ?
C37 N34 C36 C35 174.8(17) . . . . ?
C38 N34 C36 C35 5(3) . . . . ?
N31 C35 C36 N32 -152(2) . . . . ?
C34 C35 C36 N32 28(3) . . . . ?
N31 C35 C36 N34 31(3) . . . . ?
C34 C35 C36 N34 -149(2) . . . . ?
N32 N33 C37 N34 1(2) . . . . ?
N32 N33 C37 S21 176.3(15) . . . . ?
C36 N34 C37 N33 1(2) . . . . ?
C38 N34 C37 N33 171.7(16) . . . . ?
C36 N34 C37 S21 -174.6(16) . . . . ?
C38 N34 C37 S21 -4(3) . . . . ?
Hg2 S21 C37 N33 117.8(19) . . . . ?
Hg2 S21 C37 N34 -67(2) . . . . ?
C45 N41 C41 C42 -2(3) . . . . ?
N41 C41 C42 C43 0(4) . . . . ?
C41 C42 C43 C44 -1(4) . . . . ?
C42 C43 C44 C45 3(4) . . . . ?
C43 C44 C45 N41 -5(4) . . . . ?
C43 C44 C45 C46 178(2) . . . . ?
C41 N41 C45 C44 5(3) . . . . ?
C41 N41 C45 C46 -178.3(18) . . . . ?
N43 N42 C46 N44 2(2) . . . . ?
N43 N42 C46 C45 -179.8(17) . . . . ?
C47 N44 C46 N42 -2(2) . . . . ?
C48 N44 C46 N42 177.8(19) . . . . ?
C47 N44 C46 C45 -179.9(19) . . . . ?
C48 N44 C46 C45 0(3) . . . . ?
C44 C45 C46 N42 -13(3) . . . . ?
N41 C45 C46 N42 169.9(19) . . . . ?
C44 C45 C46 N44 165(2) . . . . ?
N41 C45 C46 N44 -12(3) . . . . ?
N42 N43 C47 N44 1(2) . . . . ?
N42 N43 C47 S22 -174.4(15) . . . . ?
C46 N44 C47 N43 1(2) . . . . ?
C48 N44 C47 N43 -178.9(18) . . . . ?
C46 N44 C47 S22 175.6(15) . . . . ?
C48 N44 C47 S22 -4(3) . . . . ?
Hg2 S22 C47 N43 -113.8(17) . . . . ?
Hg2 S22 C47 N44 72.2(18) . . . . ?

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
N13 H13 Br21 0.86 2.51 3.340(15) 161.3 .
N23 H23 O2 0.86 1.90 2.75(2) 172.2 .
C11 H11 Br11 0.93 2.98 3.90(2) 174.6 2_656
C18 H18A S21 0.96 2.95 3.883(18) 163.4 1_455
C18 H18B N11 0.96 2.53 3.04(2) 113.6 .
C18 H18B N22 0.96 2.63 3.45(3) 144.1 2_656
C21 H21 Br21 0.93 3.05 3.82(2) 140.6 1_545
C24 H24 Br22 0.93 3.18 3.75(2) 121.5 2_756
C28 H28B N21 0.96 2.43 2.94(3) 113.0 .
N33 H33 Br11 0.86 2.56 3.405(16) 166.8 1_655
N43 H43 O1 0.86 1.83 2.69(2) 174.6 .
C31 H31 Br21 0.93 3.01 3.92(2) 168.6 2_765
C32 H32 N21 0.93 2.65 3.56(3) 165.8 2_755
C38 H38C S21 0.96 2.73 3.222(17) 112.2 .
C48 H48B N41 0.96 2.45 2.91(3) 108.9 .

_refine_diff_density_max         2.294
_refine_diff_density_min         -2.479
_refine_diff_density_rms         0.384

####################################################################### 
# 
# 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_00gs28
_database_code_depnum_ccdc_archive 'CCDC 1452054'
_audit_update_record             
;
2016-02-06 deposited with the CCDC.
2016-04-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H38 Cl4 Hg3 N16 S4'
_chemical_formula_sum            'C36 H38 Cl4 Hg3 N16 S4'
_chemical_formula_weight         1566.63

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Hg Hg -2.3894 9.2266 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_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                   9.726(2)
_cell_length_b                   10.608(2)
_cell_length_c                   12.611(3)
_cell_angle_alpha                104.613(4)
_cell_angle_beta                 109.647(4)
_cell_angle_gamma                95.734(4)
_cell_volume                     1161.1(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1005
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      26.36

_exptl_crystal_description       prism
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.240
_exptl_crystal_F_000             738
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    10.351
_shelx_estimated_absorpt_T_min   0.107
_shelx_estimated_absorpt_T_max   0.370
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4643
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'SMART1000 CCD Bruker'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12171
_diffrn_reflns_av_unetI/netI     0.0478
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.800
_diffrn_reflns_theta_max         26.410
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4717
_reflns_number_gt                3632
_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       'SMART Software (Bruker, 1997)'
_computing_cell_refinement       'SMART Software (Bruker, 1997)'
_computing_data_reduction        'SAINT Software (Bruker, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'PLATON (Spek, 2000)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_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)+(0.0294P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4717
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0291
_refine_ls_wR_factor_ref         0.0665
_refine_ls_wR_factor_gt          0.0614
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_restrained_S_all      0.978
_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
Hg1 Hg 0.0000 0.0000 0.0000 0.03908(9) Uani 1 2 d S . P . .
Hg2 Hg 0.36130(2) 0.19439(2) 0.05033(2) 0.04342(8) Uani 1 1 d . . . . .
Cl1 Cl 0.21883(16) 0.25707(14) 0.18435(11) 0.0486(4) Uani 1 1 d . . . . .
Cl2 Cl 0.18394(19) 0.10989(16) -0.15275(11) 0.0639(5) Uani 1 1 d . . . . .
S1 S 0.14784(15) -0.16291(13) 0.01040(11) 0.0410(3) Uani 1 1 d . . . . .
S2 S 0.57021(17) 0.36612(15) 0.08027(13) 0.0522(4) Uani 1 1 d . . . . .
N11 N 0.5818(5) -0.1189(4) 0.4541(3) 0.0406(11) Uani 1 1 d . . . . .
N12 N 0.5369(5) 0.0473(4) 0.2302(3) 0.0365(10) Uani 1 1 d . . . . .
N13 N 0.4124(5) 0.0192(4) 0.1280(3) 0.0366(10) Uani 1 1 d . . . . .
N14 N 0.3800(4) -0.1246(4) 0.2196(3) 0.0315(9) Uani 1 1 d . . . . .
N21 N 1.1653(5) 0.5720(5) 0.4026(3) 0.0505(13) Uani 1 1 d . . . . .
N22 N 0.8838(5) 0.2791(4) 0.3232(3) 0.0385(10) Uani 1 1 d . . . . .
N23 N 0.7450(5) 0.2546(4) 0.2391(3) 0.0360(10) Uani 1 1 d . . . . .
H23 H 0.683(6) 0.197(5) 0.244(4) 0.043 Uiso 1 1 d . U . . .
N24 N 0.8543(5) 0.4413(4) 0.2414(3) 0.0330(9) Uani 1 1 d . . . . .
C11 C 0.6774(7) -0.1139(5) 0.5603(4) 0.0483(15) Uani 1 1 d . . . . .
H11 H 0.6471 -0.1659 0.6010 0.058 Uiso 1 1 d R U . . .
C12 C 0.8188(7) -0.0358(5) 0.6129(4) 0.0489(15) Uani 1 1 d . . . . .
H12 H 0.8825 -0.0357 0.6869 0.059 Uiso 1 1 d R U . . .
C13 C 0.8635(7) 0.0421(6) 0.5535(4) 0.0511(15) Uani 1 1 d . . . . .
H13 H 0.9577 0.0967 0.5872 0.061 Uiso 1 1 d R U . . .
C14 C 0.7667(6) 0.0379(5) 0.4437(4) 0.0461(14) Uani 1 1 d . . . . .
H14 H 0.7951 0.0879 0.4008 0.055 Uiso 1 1 d R U . . .
C15 C 0.6264(6) -0.0420(5) 0.3983(4) 0.0348(12) Uani 1 1 d . . . . .
C16 C 0.5168(5) -0.0419(5) 0.2833(4) 0.0318(11) Uani 1 1 d . . . . .
C17 C 0.3192(5) -0.0823(5) 0.1227(4) 0.0314(11) Uani 1 1 d . . . . .
C18 C 0.3099(6) -0.2386(5) 0.2417(5) 0.0419(13) Uani 1 1 d . . . . .
H18A H 0.2032 -0.2569 0.1978 0.050 Uiso 1 1 d R U . . .
H18B H 0.3267 -0.2164 0.3251 0.050 Uiso 1 1 d R U . . .
C19 C 0.3689(7) -0.3598(5) 0.2071(5) 0.0555(17) Uani 1 1 d . . . . .
H19A H 0.3422 -0.3883 0.1230 0.083 Uiso 1 1 d R U . . .
H19B H 0.3271 -0.4293 0.2302 0.083 Uiso 1 1 d R U . . .
H19C H 0.4755 -0.3403 0.2457 0.083 Uiso 1 1 d R U . . .
C21 C 1.3041(7) 0.6261(6) 0.4819(5) 0.0562(17) Uani 1 1 d . . . . .
H21 H 1.3502 0.7064 0.4803 0.067 Uiso 1 1 d R U . . .
C22 C 1.3828(6) 0.5715(6) 0.5651(4) 0.0516(15) Uani 1 1 d . . . . .
H22 H 1.4789 0.6131 0.6181 0.062 Uiso 1 1 d R U . . .
C23 C 1.3155(7) 0.4548(6) 0.5671(5) 0.0568(16) Uani 1 1 d . . . . .
H23A H 1.3658 0.4146 0.6221 0.068 Uiso 1 1 d R U . . .
C24 C 1.1728(6) 0.3952(6) 0.4881(5) 0.0499(15) Uani 1 1 d . . . . .
H24 H 1.1248 0.3158 0.4897 0.060 Uiso 1 1 d R U . . .
C25 C 1.1038(6) 0.4561(5) 0.4073(4) 0.0367(12) Uani 1 1 d . . . . .
C26 C 0.9497(6) 0.3930(5) 0.3231(4) 0.0322(11) Uani 1 1 d . . . . .
C27 C 0.7229(6) 0.3498(5) 0.1884(4) 0.0336(11) Uani 1 1 d . . . . .
C28 C 0.8774(7) 0.5662(5) 0.2130(5) 0.0489(15) Uani 1 1 d . . . . .
H28A H 0.9483 0.6343 0.2827 0.059 Uiso 1 1 d R U . . .
H28B H 0.7840 0.5963 0.1895 0.059 Uiso 1 1 d R U . . .
C29 C 0.9355(8) 0.5457(6) 0.1139(5) 0.067(2) Uani 1 1 d . . . . .
H29A H 1.0333 0.5259 0.1405 0.100 Uiso 1 1 d R U . . .
H29B H 0.9404 0.6252 0.0910 0.100 Uiso 1 1 d R U . . .
H29C H 0.8697 0.4730 0.0475 0.100 Uiso 1 1 d 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
Hg1 S1 2.3570(15) . y
Hg1 S1 2.3570(14) 2 y
Hg1 Cl1 3.1121(13) . y
Hg1 Cl2 3.3623(18) . y
Hg1 Hg2 3.6600(8) . y
Hg2 N13 2.332(4) . y
Hg2 Cl2 2.4291(13) . y
Hg2 S2 2.4469(14) . y
Hg2 Cl1 2.5319(15) . y
S1 C17 1.741(5) . ?
S2 C27 1.704(5) . ?
N11 C15 1.332(6) . ?
N11 C11 1.334(6) . ?
N12 C16 1.323(6) . ?
N12 N13 1.379(5) . ?
N13 C17 1.308(6) . ?
N14 C16 1.371(6) . ?
N14 C17 1.374(6) . ?
N14 C18 1.462(6) . ?
N21 C25 1.337(6) . ?
N21 C21 1.342(7) . ?
N22 C26 1.310(6) . ?
N22 N23 1.358(5) . ?
N23 C27 1.324(6) . ?
N23 H23 0.84(5) . ?
N24 C27 1.368(6) . ?
N24 C26 1.379(6) . ?
N24 C28 1.473(6) . ?
C11 C12 1.378(8) . ?
C11 H11 0.9300 . ?
C12 C13 1.375(8) . ?
C12 H12 0.9300 . ?
C13 C14 1.376(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.381(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.483(6) . ?
C18 C19 1.486(8) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C21 C22 1.370(8) . ?
C21 H21 0.9300 . ?
C22 C23 1.351(8) . ?
C22 H22 0.9300 . ?
C23 C24 1.377(7) . ?
C23 H23A 0.9300 . ?
C24 C25 1.365(7) . ?
C24 H24 0.9300 . ?
C25 C26 1.481(7) . ?
C28 C29 1.513(8) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 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
S1 Hg1 S1 180.0 . 2 y
S1 Hg1 Cl1 103.12(4) . . y
S1 Hg1 Cl1 76.88(4) 2 . y
S1 Hg1 Cl2 86.95(5) . . y
S1 Hg1 Cl2 93.05(5) 2 . y
Cl1 Hg1 Cl2 76.77(4) . . y
S1 Hg1 Hg2 79.11(4) . . ?
S1 Hg1 Hg2 100.89(4) 2 . ?
Cl1 Hg1 Hg2 42.96(3) . . ?
Cl2 Hg1 Hg2 40.19(2) . . ?
N13 Hg2 Cl2 110.24(10) . . y
N13 Hg2 S2 118.53(11) . . y
Cl2 Hg2 S2 113.58(5) . . y
N13 Hg2 Cl1 87.64(11) . . y
Cl2 Hg2 Cl1 108.44(6) . . y
S2 Hg2 Cl1 115.51(5) . . y
N13 Hg2 Hg1 73.74(10) . . ?
Cl2 Hg2 Hg1 63.29(4) . . ?
S2 Hg2 Hg1 166.56(4) . . ?
Cl1 Hg2 Hg1 56.90(3) . . ?
Hg2 Cl1 Hg1 80.13(4) . . ?
Hg2 Cl2 Hg1 76.51(4) . . ?
C17 S1 Hg1 105.55(17) . . ?
C27 S2 Hg2 107.48(16) . . ?
C15 N11 C11 117.4(5) . . ?
C16 N12 N13 107.0(4) . . ?
C17 N13 N12 108.5(4) . . ?
C17 N13 Hg2 128.8(3) . . ?
N12 N13 Hg2 116.5(3) . . ?
C16 N14 C17 105.3(4) . . ?
C16 N14 C18 129.7(4) . . ?
C17 N14 C18 125.0(4) . . ?
C25 N21 C21 115.7(5) . . ?
C26 N22 N23 104.6(4) . . ?
C27 N23 N22 112.8(4) . . ?
C27 N23 H23 130(4) . . ?
N22 N23 H23 114(4) . . ?
C27 N24 C26 106.5(4) . . ?
C27 N24 C28 123.4(4) . . ?
C26 N24 C28 130.0(4) . . ?
N11 C11 C12 123.4(5) . . ?
N11 C11 H11 118.3 . . ?
C12 C11 H11 118.3 . . ?
C13 C12 C11 118.5(5) . . ?
C13 C12 H12 120.8 . . ?
C11 C12 H12 120.8 . . ?
C12 C13 C14 119.0(5) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?
C13 C14 C15 118.6(5) . . ?
C13 C14 H14 120.7 . . ?
C15 C14 H14 120.7 . . ?
N11 C15 C14 123.1(4) . . ?
N11 C15 C16 117.2(4) . . ?
C14 C15 C16 119.6(4) . . ?
N12 C16 N14 109.7(4) . . ?
N12 C16 C15 122.9(4) . . ?
N14 C16 C15 127.3(4) . . ?
N13 C17 N14 109.4(4) . . ?
N13 C17 S1 128.0(4) . . ?
N14 C17 S1 122.5(3) . . ?
N14 C18 C19 112.4(5) . . ?
N14 C18 H18A 109.1 . . ?
C19 C18 H18A 109.1 . . ?
N14 C18 H18B 109.1 . . ?
C19 C18 H18B 109.1 . . ?
H18A C18 H18B 107.9 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N21 C21 C22 124.7(5) . . ?
N21 C21 H21 117.7 . . ?
C22 C21 H21 117.7 . . ?
C23 C22 C21 117.5(5) . . ?
C23 C22 H22 121.2 . . ?
C21 C22 H22 121.3 . . ?
C22 C23 C24 120.3(6) . . ?
C22 C23 H23A 119.9 . . ?
C24 C23 H23A 119.9 . . ?
C25 C24 C23 118.1(5) . . ?
C25 C24 H24 121.0 . . ?
C23 C24 H24 120.9 . . ?
N21 C25 C24 123.8(5) . . ?
N21 C25 C26 118.0(5) . . ?
C24 C25 C26 118.2(5) . . ?
N22 C26 N24 110.7(4) . . ?
N22 C26 C25 120.8(4) . . ?
N24 C26 C25 128.5(4) . . ?
N23 C27 N24 105.3(4) . . ?
N23 C27 S2 130.9(4) . . ?
N24 C27 S2 123.8(3) . . ?
N24 C28 C29 110.4(5) . . ?
N24 C28 H28A 109.5 . . ?
C29 C28 H28A 109.6 . . ?
N24 C28 H28B 109.6 . . ?
C29 C28 H28B 109.6 . . ?
H28A C28 H28B 108.1 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.4 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 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
C16 N12 N13 C17 1.7(6) . . . . ?
C16 N12 N13 Hg2 156.7(3) . . . . ?
C26 N22 N23 C27 -0.6(6) . . . . ?
C15 N11 C11 C12 -1.2(9) . . . . ?
N11 C11 C12 C13 0.6(9) . . . . ?
C11 C12 C13 C14 -0.8(9) . . . . ?
C12 C13 C14 C15 1.6(9) . . . . ?
C11 N11 C15 C14 2.0(8) . . . . ?
C11 N11 C15 C16 -176.6(5) . . . . ?
C13 C14 C15 N11 -2.3(9) . . . . ?
C13 C14 C15 C16 176.2(5) . . . . ?
N13 N12 C16 N14 -1.9(6) . . . . ?
N13 N12 C16 C15 -178.6(4) . . . . ?
C17 N14 C16 N12 1.4(6) . . . . ?
C18 N14 C16 N12 178.8(5) . . . . ?
C17 N14 C16 C15 177.9(5) . . . . ?
C18 N14 C16 C15 -4.7(8) . . . . ?
N11 C15 C16 N12 167.0(5) . . . . ?
C14 C15 C16 N12 -11.6(8) . . . . ?
N11 C15 C16 N14 -9.1(8) . . . . ?
C14 C15 C16 N14 172.3(5) . . . . ?
N12 N13 C17 N14 -0.8(6) . . . . ?
Hg2 N13 C17 N14 -151.8(3) . . . . ?
N12 N13 C17 S1 -177.6(4) . . . . ?
Hg2 N13 C17 S1 31.5(7) . . . . ?
C16 N14 C17 N13 -0.3(5) . . . . ?
C18 N14 C17 N13 -177.9(4) . . . . ?
C16 N14 C17 S1 176.6(4) . . . . ?
C18 N14 C17 S1 -0.9(7) . . . . ?
Hg1 S1 C17 N13 -61.1(5) . . . . ?
Hg1 S1 C17 N14 122.6(4) . . . . ?
C16 N14 C18 C19 -78.1(6) . . . . ?
C17 N14 C18 C19 98.8(6) . . . . ?
C25 N21 C21 C22 -0.6(9) . . . . ?
N21 C21 C22 C23 0.0(10) . . . . ?
C21 C22 C23 C24 -0.3(9) . . . . ?
C22 C23 C24 C25 1.2(9) . . . . ?
C21 N21 C25 C24 1.6(8) . . . . ?
C21 N21 C25 C26 179.0(5) . . . . ?
C23 C24 C25 N21 -2.0(9) . . . . ?
C23 C24 C25 C26 -179.3(5) . . . . ?
N23 N22 C26 N24 0.7(5) . . . . ?
N23 N22 C26 C25 177.9(4) . . . . ?
C27 N24 C26 N22 -0.5(5) . . . . ?
C28 N24 C26 N22 177.9(5) . . . . ?
C27 N24 C26 C25 -177.5(5) . . . . ?
C28 N24 C26 C25 1.0(8) . . . . ?
N21 C25 C26 N22 179.8(5) . . . . ?
C24 C25 C26 N22 -2.7(7) . . . . ?
N21 C25 C26 N24 -3.6(8) . . . . ?
C24 C25 C26 N24 173.9(5) . . . . ?
N22 N23 C27 N24 0.3(6) . . . . ?
N22 N23 C27 S2 -179.7(4) . . . . ?
C26 N24 C27 N23 0.1(5) . . . . ?
C28 N24 C27 N23 -178.5(5) . . . . ?
C26 N24 C27 S2 -179.9(4) . . . . ?
C28 N24 C27 S2 1.5(7) . . . . ?
Hg2 S2 C27 N23 10.6(6) . . . . ?
Hg2 S2 C27 N24 -169.4(4) . . . . ?
C27 N24 C28 C29 -90.1(6) . . . . ?
C26 N24 C28 C29 91.7(6) . . . . ?

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
N23 H23 N12 0.84(5) 1.95(5) 2.789(6) 171(5) .
N23 H23 N13 0.84(5) 2.76(5) 3.498(6) 147(4) .
C12 H12 Cl2 0.93 2.93 3.644(6) 134.3 1_656
C14 H14 N22 0.93 2.65 3.564(7) 166.3 .
C18 H18B N11 0.97 2.41 2.938(6) 113.9 .
C19 H19A S2 0.96 3.01 3.849(6) 146.3 2_655
C28 H28A N21 0.97 2.41 2.992(7) 118.0 .

_refine_diff_density_max         0.928
_refine_diff_density_min         -1.308
_refine_diff_density_rms         0.139
####################################################################### 
# 
# 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_98gs05
_database_code_depnum_ccdc_archive 'CCDC 1452055'
_audit_update_record             
;
2016-02-06 deposited with the CCDC.
2016-04-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H18 Hg N8 S2'
_chemical_formula_sum            'C18 H18 Hg N8 S2'
_chemical_formula_weight         611.11

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Hg Hg -2.3894 9.2266 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_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                   13.282(2)
_cell_length_b                   18.980(4)
_cell_length_c                   8.270(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.328(8)
_cell_angle_gamma                90
_cell_volume                     2084.7(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9.079
_cell_measurement_theta_max      11.534

_exptl_crystal_description       prism
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.947
_exptl_crystal_F_000             1176
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    7.606
_shelx_estimated_absorpt_T_min   0.252
_shelx_estimated_absorpt_T_max   0.395
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.756
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_process_details   '(North et al., 1968)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'MACH3 Enraf Nonius'
_diffrn_measurement_method       omega
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2686
_diffrn_reflns_av_unetI/netI     0.2084
_diffrn_reflns_av_R_equivalents  0.0718
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_theta_min         2.146
_diffrn_reflns_theta_max         27.964
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2516
_reflns_number_gt                1122
_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       'CAD4-Express Software (Nonius, 1994)'
_computing_cell_refinement       'CAD4-Express Software (Nonius, 1994)'
_computing_data_reduction        'GENHKL (Kretschamer, 1997)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXS-2013 (Sheldrick, 2013)'

_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)+(0.0540P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2516
_refine_ls_number_parameters     133
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.2068
_refine_ls_R_factor_gt           0.0534
_refine_ls_wR_factor_ref         0.1321
_refine_ls_wR_factor_gt          0.1015
_refine_ls_goodness_of_fit_ref   0.945
_refine_ls_restrained_S_all      0.944
_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
Hg1 Hg 0.5000 0.46931(3) 0.2500 0.0644(3) Uani 1 2 d S T P . .
S1 S 0.3495(2) 0.48539(13) -0.1217(4) 0.0672(8) Uani 1 1 d . . . . .
N1 N 0.3246(8) 0.1899(5) -0.1862(13) 0.081(3) Uani 1 1 d . . . . .
N2 N 0.4427(7) 0.3120(4) 0.0743(11) 0.066(3) Uani 1 1 d . . . . .
N3 N 0.4339(6) 0.3842(4) 0.0671(10) 0.063(3) Uani 1 1 d . . . . .
N4 N 0.3627(7) 0.3406(4) -0.1483(10) 0.059(2) Uani 1 1 d . . . . .
C1 C 0.3175(11) 0.1174(7) -0.2025(18) 0.097(5) Uani 1 1 d . . . . .
H1 H 0.2687 0.1002 -0.2734 0.116 Uiso 1 1 calc R U . . .
C2 C 0.3732(11) 0.0707(7) -0.127(2) 0.097(5) Uani 1 1 d . . . . .
H2 H 0.3649 0.0227 -0.1456 0.116 Uiso 1 1 calc R U . . .
C3 C 0.4436(11) 0.0946(7) -0.021(2) 0.104(5) Uani 1 1 d . . . . .
H3 H 0.4830 0.0632 0.0386 0.125 Uiso 1 1 calc R U . . .
C4 C 0.4561(10) 0.1677(6) -0.0012(18) 0.093(4) Uani 1 1 d . . . . .
H4 H 0.5053 0.1856 0.0678 0.111 Uiso 1 1 calc R U . . .
C5 C 0.3948(8) 0.2113(5) -0.0852(13) 0.053(3) Uani 1 1 d . . . . .
C6 C 0.4029(7) 0.2870(5) -0.0553(12) 0.050(3) Uani 1 1 d . . . . .
C7 C 0.3856(7) 0.4009(5) -0.0663(12) 0.051(3) Uani 1 1 d . . . . .
C8 C 0.3306(11) 0.3370(8) -0.3297(17) 0.097(4) Uani 1 1 d . U . . .
H8A H 0.3533 0.3782 -0.3885 0.117 Uiso 1 1 calc R U . . .
H8B H 0.3566 0.2950 -0.3814 0.117 Uiso 1 1 calc R U . . .
C9 C 0.2250(13) 0.3352(8) -0.320(2) 0.130(6) Uani 1 1 d . . . . .
H9A H 0.2050 0.2989 -0.2458 0.195 Uiso 1 1 calc R U . . .
H9B H 0.1971 0.3254 -0.4250 0.195 Uiso 1 1 calc R U . . .
H9C H 0.2007 0.3799 -0.2826 0.195 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
Hg1 N3 2.378(7) . y
Hg1 N3 2.378(7) 2_655 y
Hg1 S1 2.426(3) 6_566 y
Hg1 S1 2.426(3) 5_665 y
Hg1 Hg1 4.2960(15) 6_566 y
S1 C7 1.735(9) . ?
S1 Hg1 2.426(3) 5_665 ?
S1 S1 4.1721(16) 6_566 y
N1 C5 1.312(12) . ?
N1 C1 1.386(15) . ?
N2 C6 1.283(12) . ?
N2 N3 1.377(11) . ?
N3 C7 1.311(11) . ?
N4 C7 1.364(12) . ?
N4 C6 1.380(12) . ?
N4 C8 1.559(15) . ?
C1 C2 1.310(17) . ?
C1 H1 0.9300 . ?
C2 C3 1.359(17) . ?
C2 H2 0.9300 . ?
C3 C4 1.406(17) . ?
C3 H3 0.9300 . ?
C4 C5 1.350(15) . ?
C4 H4 0.9300 . ?
C5 C6 1.463(13) . ?
C8 C9 1.406(17) . ?
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
N3 Hg1 N3 94.4(4) . 2_655 y
N3 Hg1 S1 102.5(2) . 6_566 y
N3 Hg1 S1 105.4(2) 2_655 6_566 y
N3 Hg1 S1 105.4(2) . 5_665 y
N3 Hg1 S1 102.5(2) 2_655 5_665 y
S1 Hg1 S1 138.49(12) 6_566 5_665 y
N3 Hg1 Hg1 142.6(2) . 6_566 ?
N3 Hg1 Hg1 64.8(2) 2_655 6_566 ?
S1 Hg1 Hg1 58.56(7) 6_566 6_566 ?
S1 Hg1 Hg1 109.23(8) 5_665 6_566 ?
C7 S1 Hg1 102.5(4) . 5_665 ?
C7 S1 S1 82.1(4) . 6_566 ?
Hg1 S1 S1 113.02(9) 5_665 6_566 ?
C5 N1 C1 114.6(11) . . ?
C6 N2 N3 107.3(8) . . ?
C7 N3 N2 108.5(8) . . ?
C7 N3 Hg1 123.2(6) . . ?
N2 N3 Hg1 128.1(6) . . ?
C7 N4 C6 104.9(7) . . ?
C7 N4 C8 125.0(9) . . ?
C6 N4 C8 127.4(9) . . ?
C2 C1 N1 125.9(12) . . ?
C2 C1 H1 117.0 . . ?
N1 C1 H1 117.0 . . ?
C1 C2 C3 117.9(12) . . ?
C1 C2 H2 121.0 . . ?
C3 C2 H2 121.0 . . ?
C2 C3 C4 118.9(13) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C5 C4 C3 118.4(12) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
N1 C5 C4 124.2(10) . . ?
N1 C5 C6 117.6(9) . . ?
C4 C5 C6 118.1(10) . . ?
N2 C6 N4 110.5(8) . . ?
N2 C6 C5 122.3(9) . . ?
N4 C6 C5 127.0(9) . . ?
N3 C7 N4 108.8(8) . . ?
N3 C7 S1 125.4(8) . . ?
N4 C7 S1 125.7(7) . . ?
C9 C8 N4 102.4(13) . . ?
C9 C8 H8A 111.3 . . ?
N4 C8 H8A 111.3 . . ?
C9 C8 H8B 111.3 . . ?
N4 C8 H8B 111.3 . . ?
H8A C8 H8B 109.2 . . ?
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
C6 N2 N3 C7 2.0(12) . . . . ?
C6 N2 N3 Hg1 -174.8(7) . . . . ?
C5 N1 C1 C2 0(2) . . . . ?
N1 C1 C2 C3 1(3) . . . . ?
C1 C2 C3 C4 -2(2) . . . . ?
C2 C3 C4 C5 2(2) . . . . ?
C1 N1 C5 C4 -0.4(19) . . . . ?
C1 N1 C5 C6 -176.7(11) . . . . ?
C3 C4 C5 N1 -1(2) . . . . ?
C3 C4 C5 C6 175.4(13) . . . . ?
N3 N2 C6 N4 -2.8(12) . . . . ?
N3 N2 C6 C5 -177.1(10) . . . . ?
C7 N4 C6 N2 2.5(12) . . . . ?
C8 N4 C6 N2 164.4(11) . . . . ?
C7 N4 C6 C5 176.6(10) . . . . ?
C8 N4 C6 C5 -21.5(18) . . . . ?
N1 C5 C6 N2 156.3(11) . . . . ?
C4 C5 C6 N2 -20.3(18) . . . . ?
N1 C5 C6 N4 -17.1(17) . . . . ?
C4 C5 C6 N4 166.3(12) . . . . ?
N2 N3 C7 N4 -0.4(12) . . . . ?
Hg1 N3 C7 N4 176.5(6) . . . . ?
N2 N3 C7 S1 175.6(8) . . . . ?
Hg1 N3 C7 S1 -7.5(14) . . . . ?
C6 N4 C7 N3 -1.2(12) . . . . ?
C8 N4 C7 N3 -163.7(10) . . . . ?
C6 N4 C7 S1 -177.2(8) . . . . ?
C8 N4 C7 S1 20.3(16) . . . . ?
Hg1 S1 C7 N3 84.8(10) 5_665 . . . ?
S1 S1 C7 N3 -27.1(9) 6_566 . . . ?
Hg1 S1 C7 N4 -99.8(9) 5_665 . . . ?
S1 S1 C7 N4 148.2(10) 6_566 . . . ?
C7 N4 C8 C9 -96.4(14) . . . . ?
C6 N4 C8 C9 105.1(14) . . . . ?

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
C1 H1 S1 0.93 2.82 3.642(12) 148.0 4_544
C9 H9A N1 0.96 2.65 3.250(19) 120.7 .

_refine_diff_density_max         0.881
_refine_diff_density_min         -1.883
_refine_diff_density_rms         0.170

_shelxl_version_number           2013-3

####################################################################### 
# 
# 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_06rr03
_database_code_depnum_ccdc_archive 'CCDC 1452056'
_audit_update_record             
;
2016-02-06 deposited with the CCDC.
2016-04-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H12 Hg N10 S2'
_chemical_formula_sum            'C14 H12 Hg N10 S2'
_chemical_formula_weight         585.05

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Hg Hg -2.3894 9.2266 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

_cell_length_a                   7.1597(2)
_cell_length_b                   6.3074(2)
_cell_length_c                   38.1938(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1724.80(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5854
_cell_measurement_theta_min      3.273
_cell_measurement_theta_max      30.330

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.253
_exptl_crystal_F_000             1112
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    9.190
_shelx_estimated_absorpt_T_min   0.120
_shelx_estimated_absorpt_T_max   0.770
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1202
_exptl_absorpt_correction_T_max  0.7700
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker, X8 KappaAPEXII'
_diffrn_measurement_method       'omega/phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28560
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -49
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_theta_min         2.133
_diffrn_reflns_theta_max         30.855
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.904
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.904
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.905
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4359
_reflns_number_gt                4098
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.977
_reflns_Friedel_fraction_max     0.907
_reflns_Friedel_fraction_full    0.997

_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 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       'APEX2 Software (Bruker, 2005)'
_computing_cell_refinement       'APEX2 Software (Bruker, 2005)'
_computing_data_reduction        'APEX2 Software (Bruker, 2005)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'PLATON (Spek, 2004)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+8.9250P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.620(9)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4359
_refine_ls_number_parameters     247
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0302
_refine_ls_R_factor_gt           0.0274
_refine_ls_wR_factor_ref         0.0547
_refine_ls_wR_factor_gt          0.0540
_refine_ls_goodness_of_fit_ref   1.200
_refine_ls_restrained_S_all      1.200
_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
Hg1 Hg 0.44625(3) 0.41373(4) 1.00290(2) 0.01335(7) Uani 1 1 d . . . . .
S1 S 0.6329(2) 0.0531(3) 0.97803(5) 0.0117(4) Uani 1 1 d . . . . .
S2 S 0.7140(3) 0.6160(3) 1.02255(5) 0.0133(4) Uani 1 1 d . . . . .
N11 N 0.7816(10) -0.0678(12) 0.83231(18) 0.0197(15) Uani 1 1 d . . . . .
N12 N 0.6519(9) 0.3576(11) 0.89062(18) 0.0156(14) Uani 1 1 d . . . . .
N13 N 0.6161(9) 0.3438(11) 0.92593(17) 0.0134(13) Uani 1 1 d . . . . .
N14 N 0.7234(9) 0.0336(10) 0.90800(17) 0.0112(12) Uani 1 1 d . . . . .
N16 N 0.8706(11) 0.2832(13) 0.78945(19) 0.0234(16) Uani 1 1 d . . . . .
N21 N 0.3978(10) -0.0705(12) 1.16532(18) 0.0187(15) Uani 1 1 d . . . . .
N22 N 0.4123(8) 0.2815(11) 1.09107(16) 0.0130(13) Uani 1 1 d . . . . .
N23 N 0.3685(9) 0.2239(11) 1.05716(16) 0.0119(12) Uani 1 1 d . . . . .
N24 N 0.2828(8) -0.0349(10) 1.09181(16) 0.0109(12) Uani 1 1 d . . . . .
N26 N 0.4584(11) 0.3107(13) 1.20188(19) 0.0240(16) Uani 1 1 d . . . . .
C11 C 0.8352(14) -0.0882(16) 0.7988(2) 0.029(2) Uani 1 1 d . . . . .
H11 H 0.8433 -0.2268 0.7892 0.034 Uiso 1 1 calc R U . . .
C12 C 0.8789(12) 0.0808(16) 0.7778(2) 0.0240(19) Uani 1 1 d . . . . .
H12 H 0.9162 0.0551 0.7543 0.029 Uiso 1 1 calc R U . . .
C14 C 0.8184(11) 0.3051(14) 0.8227(2) 0.0193(17) Uani 1 1 d . . . . .
H14 H 0.8100 0.4439 0.8322 0.023 Uiso 1 1 calc R U . . .
C15 C 0.7749(11) 0.1302(14) 0.8444(2) 0.0161(16) Uani 1 1 d . . . . .
C16 C 0.7174(10) 0.1737(12) 0.88046(19) 0.0116(14) Uani 1 1 d . . . . .
C17 C 0.6614(10) 0.1522(12) 0.9357(2) 0.0112(14) Uani 1 1 d . . . . .
C18 C 0.8015(12) -0.1798(13) 0.9097(2) 0.0185(17) Uani 1 1 d . . . . .
H18A H 0.7798 -0.2394 0.9330 0.028 Uiso 1 1 calc R U . . .
H18B H 0.9361 -0.1738 0.9051 0.028 Uiso 1 1 calc R U . . .
H18C H 0.7411 -0.2695 0.8921 0.028 Uiso 1 1 calc R U . . .
C21 C 0.4325(13) -0.0649(16) 1.1995(2) 0.0266(19) Uani 1 1 d . . . . .
H21 H 0.4346 -0.1948 1.2121 0.032 Uiso 1 1 calc R U . . .
C22 C 0.4656(13) 0.1208(17) 1.2176(2) 0.027(2) Uani 1 1 d . . . . .
H22 H 0.4943 0.1138 1.2419 0.032 Uiso 1 1 calc R U . . .
C24 C 0.4177(11) 0.3081(13) 1.1676(2) 0.0172(17) Uani 1 1 d . . . . .
H24 H 0.4059 0.4388 1.1555 0.021 Uiso 1 1 calc R U . . .
C25 C 0.3923(10) 0.1190(13) 1.1493(2) 0.0127(15) Uani 1 1 d . . . . .
C26 C 0.3613(10) 0.1233(13) 1.1112(2) 0.0120(15) Uani 1 1 d . . . . .
C27 C 0.7886(10) 0.4652(13) 1.0579(2) 0.0130(15) Uani 1 1 d . . . . .
C28 C 0.1920(11) -0.2307(14) 1.1029(2) 0.0173(16) Uani 1 1 d . . . . .
H28A H 0.0950 -0.2692 1.0860 0.026 Uiso 1 1 calc R U . . .
H28B H 0.1351 -0.2098 1.1260 0.026 Uiso 1 1 calc R U . . .
H28C H 0.2849 -0.3446 1.1043 0.026 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
Hg1 S2 2.4219(19) . y
Hg1 S1 2.4451(18) 4_455 y
Hg1 N23 2.457(6) . y
Hg1 S1 2.8040(19) . y
Hg1 Hg1 4.1330(3) 4_455 y
Hg1 Hg1 4.1330(3) 4 y
S1 C17 1.745(8) . ?
S1 Hg1 2.4452(18) 4 ?
S2 C27 1.735(8) . ?
N11 C15 1.333(11) . ?
N11 C11 1.342(11) . ?
N12 C16 1.310(10) . ?
N12 N13 1.375(9) . ?
N13 C17 1.306(10) . ?
N14 C17 1.370(10) . ?
N14 C16 1.374(10) . ?
N14 C18 1.458(10) . ?
N16 C14 1.331(11) . ?
N16 C12 1.353(13) . ?
N21 C21 1.331(11) . ?
N21 C25 1.343(11) . ?
N22 C26 1.313(10) . ?
N22 N23 1.381(9) . ?
N23 C27 1.323(11) 4_455 ?
N24 C26 1.364(10) . ?
N24 C27 1.370(10) 4_455 ?
N24 C28 1.459(10) . ?
N26 C24 1.340(11) . ?
N26 C22 1.341(13) . ?
C11 C12 1.371(14) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C14 C15 1.415(12) . ?
C14 H14 0.9500 . ?
C15 C16 1.463(11) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C21 C22 1.379(14) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C24 C25 1.395(11) . ?
C24 H24 0.9500 . ?
C25 C26 1.473(11) . ?
C27 N23 1.323(10) 4 ?
C27 N24 1.370(10) 4 ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?

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 Hg1 S1 143.27(7) . 4_455 y
S2 Hg1 N23 100.05(15) . . y
S1 Hg1 N23 99.30(15) 4_455 . y
S2 Hg1 S1 98.92(6) . . y
S1 Hg1 S1 112.03(6) 4_455 . y
N23 Hg1 S1 89.90(16) . . y
S2 Hg1 Hg1 161.59(5) . 4_455 ?
S1 Hg1 Hg1 41.24(5) 4_455 4_455 ?
N23 Hg1 Hg1 63.92(15) . 4_455 ?
S1 Hg1 Hg1 90.43(4) . 4_455 ?
S2 Hg1 Hg1 65.02(5) . 4 ?
S1 Hg1 Hg1 146.87(5) 4_455 4 ?
N23 Hg1 Hg1 87.28(15) . 4 ?
S1 Hg1 Hg1 35.09(4) . 4 ?
Hg1 Hg1 Hg1 120.034(12) 4_455 4 ?
C17 S1 Hg1 102.8(2) . 4 ?
C17 S1 Hg1 94.5(3) . . ?
Hg1 S1 Hg1 103.67(7) 4 . ?
C27 S2 Hg1 101.3(3) . . ?
C15 N11 C11 115.5(8) . . ?
C16 N12 N13 107.5(6) . . ?
C17 N13 N12 107.0(6) . . ?
C17 N14 C16 103.3(6) . . ?
C17 N14 C18 126.4(7) . . ?
C16 N14 C18 129.7(7) . . ?
C14 N16 C12 115.1(8) . . ?
C21 N21 C25 115.3(8) . . ?
C26 N22 N23 106.6(6) . . ?
C27 N23 N22 108.4(6) 4_455 . ?
C27 N23 Hg1 123.7(5) 4_455 . ?
N22 N23 Hg1 127.7(5) . . ?
C26 N24 C27 105.5(6) . 4_455 ?
C26 N24 C28 130.1(7) . . ?
C27 N24 C28 124.1(7) 4_455 . ?
C24 N26 C22 115.7(8) . . ?
N11 C11 C12 123.3(9) . . ?
N11 C11 H11 118.4 . . ?
C12 C11 H11 118.4 . . ?
N16 C12 C11 122.1(8) . . ?
N16 C12 H12 119.0 . . ?
C11 C12 H12 119.0 . . ?
N16 C14 C15 122.7(8) . . ?
N16 C14 H14 118.7 . . ?
C15 C14 H14 118.7 . . ?
N11 C15 C14 121.3(7) . . ?
N11 C15 C16 120.8(7) . . ?
C14 C15 C16 117.9(8) . . ?
N12 C16 N14 110.7(7) . . ?
N12 C16 C15 123.0(7) . . ?
N14 C16 C15 126.2(7) . . ?
N13 C17 N14 111.4(7) . . ?
N13 C17 S1 124.5(6) . . ?
N14 C17 S1 123.9(6) . . ?
N14 C18 H18A 109.5 . . ?
N14 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N14 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N21 C21 C22 123.1(9) . . ?
N21 C21 H21 118.5 . . ?
C22 C21 H21 118.5 . . ?
N26 C22 C21 121.9(8) . . ?
N26 C22 H22 119.1 . . ?
C21 C22 H22 119.1 . . ?
N26 C24 C25 121.9(8) . . ?
N26 C24 H24 119.0 . . ?
C25 C24 H24 119.0 . . ?
N21 C25 C24 122.0(7) . . ?
N21 C25 C26 118.0(7) . . ?
C24 C25 C26 120.0(7) . . ?
N22 C26 N24 110.6(7) . . ?
N22 C26 C25 123.5(7) . . ?
N24 C26 C25 125.9(7) . . ?
N23 C27 N24 108.8(6) 4 4 ?
N23 C27 S2 127.7(6) 4 . ?
N24 C27 S2 123.4(6) 4 . ?
N24 C28 H28A 109.5 . . ?
N24 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
N24 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 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
C16 N12 N13 C17 0.0(8) . . . . ?
C26 N22 N23 C27 1.4(8) . . . 4_455 ?
C26 N22 N23 Hg1 -173.3(5) . . . . ?
C15 N11 C11 C12 -0.7(14) . . . . ?
C14 N16 C12 C11 0.4(13) . . . . ?
N11 C11 C12 N16 -0.1(15) . . . . ?
C12 N16 C14 C15 0.1(12) . . . . ?
C11 N11 C15 C14 1.2(12) . . . . ?
C11 N11 C15 C16 179.6(8) . . . . ?
N16 C14 C15 N11 -1.0(13) . . . . ?
N16 C14 C15 C16 -179.4(8) . . . . ?
N13 N12 C16 N14 1.2(8) . . . . ?
N13 N12 C16 C15 -178.8(7) . . . . ?
C17 N14 C16 N12 -1.8(8) . . . . ?
C18 N14 C16 N12 -173.6(7) . . . . ?
C17 N14 C16 C15 178.1(7) . . . . ?
C18 N14 C16 C15 6.3(12) . . . . ?
N11 C15 C16 N12 -157.7(8) . . . . ?
C14 C15 C16 N12 20.7(11) . . . . ?
N11 C15 C16 N14 22.3(12) . . . . ?
C14 C15 C16 N14 -159.2(7) . . . . ?
N12 N13 C17 N14 -1.2(8) . . . . ?
N12 N13 C17 S1 -177.4(5) . . . . ?
C16 N14 C17 N13 1.9(8) . . . . ?
C18 N14 C17 N13 174.0(7) . . . . ?
C16 N14 C17 S1 178.1(5) . . . . ?
C18 N14 C17 S1 -9.8(11) . . . . ?
Hg1 S1 C17 N13 -99.6(6) 4 . . . ?
Hg1 S1 C17 N13 5.6(7) . . . . ?
Hg1 S1 C17 N14 84.7(6) 4 . . . ?
Hg1 S1 C17 N14 -170.2(6) . . . . ?
C25 N21 C21 C22 -1.6(13) . . . . ?
C24 N26 C22 C21 -0.2(14) . . . . ?
N21 C21 C22 N26 2.4(15) . . . . ?
C22 N26 C24 C25 -2.6(12) . . . . ?
C21 N21 C25 C24 -1.2(11) . . . . ?
C21 N21 C25 C26 177.8(7) . . . . ?
N26 C24 C25 N21 3.4(12) . . . . ?
N26 C24 C25 C26 -175.5(7) . . . . ?
N23 N22 C26 N24 -1.0(8) . . . . ?
N23 N22 C26 C25 177.2(7) . . . . ?
C27 N24 C26 N22 0.2(8) 4_455 . . . ?
C28 N24 C26 N22 -174.0(7) . . . . ?
C27 N24 C26 C25 -177.9(7) 4_455 . . . ?
C28 N24 C26 C25 7.9(12) . . . . ?
N21 C25 C26 N22 -156.7(7) . . . . ?
C24 C25 C26 N22 22.3(11) . . . . ?
N21 C25 C26 N24 21.1(11) . . . . ?
C24 C25 C26 N24 -159.9(7) . . . . ?
Hg1 S2 C27 N23 70.6(7) . . . 4 ?
Hg1 S2 C27 N24 -113.8(6) . . . 4 ?

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
C12 H12 N26 0.95 2.68 3.558(11) 153.8 3_644
C18 H18A S1 0.98 2.73 3.229(9) 112.0 .
C18 H18B N12 0.98 2.58 3.310(11) 131.0 4
C18 H18B N13 0.98 2.57 3.154(11) 117.9 4
C18 H18C N12 0.98 2.44 3.192(11) 133.5 1_545
C28 H28A N24 0.98 2.56 3.309(10) 132.9 4_445
C28 H28B N21 0.98 2.66 3.418(11) 134.7 4_445
C28 H28C N22 0.98 2.58 3.487(11) 154.2 1_545

_refine_diff_density_max         3.041
_refine_diff_density_min         -3.930
_refine_diff_density_rms         0.176

####################################################################### 
# 
# 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_05rr08
_database_code_depnum_ccdc_archive 'CCDC 1452057'
_audit_update_record             
;
2016-02-06 deposited with the CCDC.
2016-04-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H16 Hg N10 S2'
_chemical_formula_sum            'C16 H16 Hg N10 S2'
_chemical_formula_weight         613.10

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Hg Hg -2.3894 9.2266 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   14.646(16)
_cell_length_b                   10.045(11)
_cell_length_c                   15.852(17)
_cell_angle_alpha                90
_cell_angle_beta                 116.057(16)
_cell_angle_gamma                90
_cell_volume                     2095(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1255
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      23.735

_exptl_crystal_description       plate
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.944
_exptl_crystal_F_000             1176
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    7.571
_shelx_estimated_absorpt_T_min   0.377
_shelx_estimated_absorpt_T_max   0.619
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.609
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Smart CCD-1000'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17778
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.580
_diffrn_reflns_theta_max         26.422
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4297
_reflns_number_gt                3074
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 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       'SMART Software (Bruker, 1997)'
_computing_cell_refinement       'SMART Software (Bruker, 1997)'
_computing_data_reduction        'SAINT Software (Bruker, 1997)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_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)+(0.0252P)²+1.0608P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4297
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0306
_refine_ls_wR_factor_ref         0.0651
_refine_ls_wR_factor_gt          0.0597
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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
Hg1 Hg 0.22559(2) 0.55052(2) 0.66635(2) 0.03755(8) Uani 1 1 d . . . . .
S1 S 0.21587(13) 0.44511(16) 0.52850(11) 0.0548(4) Uani 1 1 d . . . . .
S2 S 0.28020(11) 0.63083(13) 0.82175(9) 0.0403(3) Uani 1 1 d . . . . .
N11 N 0.4597(4) 0.5912(6) 0.3489(4) 0.0646(15) Uani 1 1 d . . . . .
N12 N 0.3903(4) 0.7297(5) 0.5217(4) 0.0659(15) Uani 1 1 d . . . . .
N13 N 0.3299(4) 0.6705(5) 0.5582(4) 0.0603(14) Uani 1 1 d . . . . .
N14 N 0.3301(4) 0.5446(5) 0.4449(3) 0.0559(13) Uani 1 1 d . . . . .
N16 N 0.5202(6) 0.8520(8) 0.3435(6) 0.116(3) Uani 1 1 d . . . . .
N21 N -0.0584(3) 0.2000(5) 0.6482(3) 0.0460(12) Uani 1 1 d . . . . .
N22 N 0.1206(3) 0.7729(4) 0.5988(3) 0.0393(11) Uani 1 1 d . . . . .
N23 N 0.1658(3) 0.8691(4) 0.6676(3) 0.0399(11) Uani 1 1 d . . . . .
N24 N 0.1320(3) 0.9600(4) 0.5300(3) 0.0326(9) Uani 1 1 d . . . . .
N26 N 0.0623(3) 0.4195(4) 0.6550(3) 0.0449(12) Uani 1 1 d . . . . .
C11 C 0.5083(5) 0.6267(8) 0.2992(5) 0.068(2) Uani 1 1 d . . . . .
H11 H 0.5234 0.5617 0.2655 0.082 Uiso 1 1 calc R U . . .
C12 C 0.5369(6) 0.7532(10) 0.2953(5) 0.087(3) Uani 1 1 d . . . . .
H12 H 0.5689 0.7745 0.2577 0.104 Uiso 1 1 d R U . . .
C14 C 0.4730(6) 0.8162(8) 0.3963(6) 0.093(3) Uani 1 1 d . . . . .
H14 H 0.4614 0.8799 0.4331 0.112 Uiso 1 1 calc R U . . .
C15 C 0.4418(5) 0.6871(7) 0.3967(4) 0.0548(16) Uani 1 1 d . . . . .
C16 C 0.3877(4) 0.6542(6) 0.4535(4) 0.0509(15) Uani 1 1 d . . . . .
C17 C 0.2939(4) 0.5603(6) 0.5102(4) 0.0437(13) Uani 1 1 d . . . . .
C18 C 0.3212(9) 0.4046(14) 0.3865(7) 0.146(5) Uani 1 1 d . . . . .
H18A H 0.3807 0.3876 0.3761 0.175 Uiso 1 1 d R U . . .
H18B H 0.3065 0.3279 0.4156 0.175 Uiso 1 1 d R U . . .
C19 C 0.2454(10) 0.4411(17) 0.3113(10) 0.202(8) Uani 1 1 d . . . . .
H19A H 0.1864 0.4440 0.3230 0.303 Uiso 1 1 d R U . . .
H19B H 0.2339 0.3798 0.2612 0.303 Uiso 1 1 d R U . . .
H19C H 0.2583 0.5282 0.2940 0.303 Uiso 1 1 d R U . . .
C21 C -0.0057(4) 0.2688(6) 0.7272(4) 0.0533(16) Uani 1 1 d . . . . .
H21 H -0.0092 0.2424 0.7819 0.064 Uiso 1 1 d R U . . .
C22 C 0.0537(4) 0.3766(6) 0.7311(4) 0.0478(15) Uani 1 1 d . . . . .
H22 H 0.0886 0.4210 0.7878 0.057 Uiso 1 1 d R U . . .
C24 C 0.0107(4) 0.3521(5) 0.5761(4) 0.0388(12) Uani 1 1 d . . . . .
H24 H 0.0151 0.3790 0.5219 0.047 Uiso 1 1 d R U . . .
C25 C -0.0488(4) 0.2425(5) 0.5718(3) 0.0332(12) Uani 1 1 d . . . . .
C26 C 0.1017(4) 0.8270(5) 0.5180(3) 0.0337(12) Uani 1 1 d . . . . .
C27 C 0.3286(4) 0.4787(5) 0.8751(3) 0.0302(11) Uani 1 1 d . . . . .
C28 C 0.1287(5) 1.0572(6) 0.4600(4) 0.0519(15) Uani 1 1 d . . . . .
H28A H 0.1223 1.1462 0.4807 0.062 Uiso 1 1 d R U . . .
H28B H 0.0694 1.0402 0.4012 0.062 Uiso 1 1 d R U . . .
C29 C 0.2224(6) 1.0503(8) 0.4448(5) 0.087(3) Uani 1 1 d . . . . .
H29A H 0.2812 1.0665 0.5030 0.130 Uiso 1 1 d R U . . .
H29B H 0.2189 1.1163 0.3996 0.130 Uiso 1 1 d R U . . .
H29C H 0.2273 0.9635 0.4218 0.130 Uiso 1 1 d 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
Hg1 S2 2.372(3) . y
Hg1 S1 2.376(3) . y
Hg1 N22 2.656(5) . y
Hg1 N26 2.666(5) . y
S1 C17 1.739(6) . ?
S2 C27 1.739(5) . ?
N11 C11 1.321(8) . ?
N11 C15 1.322(8) . ?
N12 C16 1.308(7) . ?
N12 N13 1.386(7) . ?
N13 C17 1.315(7) . ?
N14 C16 1.357(7) . ?
N14 C17 1.362(7) . ?
N14 C18 1.658(14) . ?
N16 C12 1.339(10) . ?
N16 C14 1.348(9) . ?
N21 C21 1.339(7) . ?
N21 C25 1.348(6) . ?
N22 C26 1.304(6) . ?
N22 N23 1.389(6) . ?
N23 C27 1.314(6) 2_556 ?
N24 C27 1.367(6) 2_556 ?
N24 C26 1.394(6) . ?
N24 C28 1.463(6) . ?
N26 C24 1.328(6) . ?
N26 C22 1.338(7) . ?
C11 C12 1.348(10) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C14 C15 1.377(10) . ?
C14 H14 0.9300 . ?
C15 C16 1.473(8) . ?
C18 C19 1.275(15) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C21 C22 1.373(8) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C24 C25 1.387(7) . ?
C24 H24 0.9300 . ?
C25 C26 1.465(7) 3_566 ?
C26 C25 1.465(7) 3_566 ?
C27 N23 1.314(6) 2_546 ?
C27 N24 1.367(6) 2_546 ?
C28 C29 1.497(9) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 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 Hg1 S1 164.45(6) . . y
S2 Hg1 N22 90.25(10) . . y
S1 Hg1 N22 102.33(11) . . y
S2 Hg1 N26 96.95(11) . . y
S1 Hg1 N26 91.64(11) . . y
N22 Hg1 N26 92.55(15) . . y
C17 S1 Hg1 94.5(2) . . y
C27 S2 Hg1 94.90(18) . . y
C11 N11 C15 116.1(6) . . ?
C16 N12 N13 107.7(5) . . ?
C17 N13 N12 106.6(5) . . ?
C16 N14 C17 105.2(5) . . ?
C16 N14 C18 129.5(5) . . ?
C17 N14 C18 124.1(5) . . ?
C12 N16 C14 115.4(7) . . ?
C21 N21 C25 115.6(5) . . ?
C26 N22 N23 107.7(4) . . ?
C26 N22 Hg1 125.6(3) . . ?
N23 N22 Hg1 106.1(3) . . ?
C27 N23 N22 107.1(4) 2_556 . ?
C27 N24 C26 103.8(4) 2_556 . ?
C27 N24 C28 126.9(4) 2_556 . ?
C26 N24 C28 129.3(4) . . ?
C24 N26 C22 116.4(5) . . ?
C24 N26 Hg1 116.0(4) . . ?
C22 N26 Hg1 122.4(3) . . ?
N11 C11 C12 122.8(7) . . ?
N11 C11 H11 118.6 . . ?
C12 C11 H11 118.6 . . ?
N16 C12 C11 122.3(7) . . ?
N16 C12 H12 117.7 . . ?
C11 C12 H12 120.1 . . ?
N16 C14 C15 121.1(8) . . ?
N16 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
N11 C15 C14 122.2(6) . . ?
N11 C15 C16 118.8(6) . . ?
C14 C15 C16 118.9(7) . . ?
N12 C16 N14 110.1(5) . . ?
N12 C16 C15 123.1(6) . . ?
N14 C16 C15 126.8(6) . . ?
N13 C17 N14 110.3(5) . . ?
N13 C17 S1 126.0(4) . . ?
N14 C17 S1 123.6(4) . . ?
C19 C18 N14 95.8(13) . . ?
C19 C18 H18A 111.7 . . ?
N14 C18 H18A 112.9 . . ?
C19 C18 H18B 112.9 . . ?
N14 C18 H18B 112.8 . . ?
H18A C18 H18B 110.2 . . ?
C18 C19 H19A 108.5 . . ?
C18 C19 H19B 110.7 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.2 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N21 C21 C22 122.9(5) . . ?
N21 C21 H21 118.7 . . ?
C22 C21 H21 118.5 . . ?
N26 C22 C21 121.5(5) . . ?
N26 C22 H22 119.2 . . ?
C21 C22 H22 119.4 . . ?
N26 C24 C25 122.4(5) . . ?
N26 C24 H24 118.7 . . ?
C25 C24 H24 118.9 . . ?
N21 C25 C24 121.2(5) . . ?
N21 C25 C26 120.2(4) . 3_566 ?
C24 C25 C26 118.6(5) . 3_566 ?
N22 C26 N24 110.3(4) . . ?
N22 C26 C25 123.3(4) . 3_566 ?
N24 C26 C25 126.2(4) . 3_566 ?
N23 C27 N24 111.1(4) 2_546 2_546 ?
N23 C27 S2 126.2(4) 2_546 . ?
N24 C27 S2 122.7(4) 2_546 . ?
N24 C28 C29 111.4(5) . . ?
N24 C28 H28A 109.6 . . ?
C29 C28 H28A 109.2 . . ?
N24 C28 H28B 109.2 . . ?
C29 C28 H28B 109.4 . . ?
H28A C28 H28B 108.0 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.6 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.3 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 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
C16 N12 N13 C17 0.5(7) . . . . ?
C26 N22 N23 C27 0.6(6) . . . 2_556 ?
Hg1 N22 N23 C27 137.3(3) . . . 2_556 ?
C15 N11 C11 C12 -1.2(11) . . . . ?
C14 N16 C12 C11 0.1(14) . . . . ?
N11 C11 C12 N16 1.7(13) . . . . ?
C12 N16 C14 C15 -2.2(14) . . . . ?
C11 N11 C15 C14 -0.9(10) . . . . ?
C11 N11 C15 C16 179.9(6) . . . . ?
N16 C14 C15 N11 2.7(13) . . . . ?
N16 C14 C15 C16 -178.1(7) . . . . ?
N13 N12 C16 N14 -1.8(7) . . . . ?
N13 N12 C16 C15 178.8(6) . . . . ?
C17 N14 C16 N12 2.3(7) . . . . ?
C18 N14 C16 N12 -165.8(7) . . . . ?
C17 N14 C16 C15 -178.3(6) . . . . ?
C18 N14 C16 C15 13.6(11) . . . . ?
N11 C15 C16 N12 160.8(6) . . . . ?
C14 C15 C16 N12 -18.4(10) . . . . ?
N11 C15 C16 N14 -18.5(10) . . . . ?
C14 C15 C16 N14 162.3(7) . . . . ?
N12 N13 C17 N14 1.0(7) . . . . ?
N12 N13 C17 S1 178.4(4) . . . . ?
C16 N14 C17 N13 -2.0(7) . . . . ?
C18 N14 C17 N13 166.9(7) . . . . ?
C16 N14 C17 S1 -179.5(4) . . . . ?
C18 N14 C17 S1 -10.6(9) . . . . ?
Hg1 S1 C17 N13 -6.2(5) . . . . ?
Hg1 S1 C17 N14 170.9(5) . . . . ?
C16 N14 C18 C19 -93.3(11) . . . . ?
C17 N14 C18 C19 100.5(10) . . . . ?
C25 N21 C21 C22 0.6(9) . . . . ?
C24 N26 C22 C21 -0.2(8) . . . . ?
Hg1 N26 C22 C21 -153.5(4) . . . . ?
N21 C21 C22 N26 0.0(9) . . . . ?
C22 N26 C24 C25 -0.3(8) . . . . ?
Hg1 N26 C24 C25 154.7(4) . . . . ?
C21 N21 C25 C24 -1.1(8) . . . . ?
C21 N21 C25 C26 178.9(5) . . . 3_566 ?
N26 C24 C25 N21 1.0(8) . . . . ?
N26 C24 C25 C26 -179.1(5) . . . 3_566 ?
N23 N22 C26 N24 -0.9(6) . . . . ?
Hg1 N22 C26 N24 -126.7(4) . . . . ?
N23 N22 C26 C25 -176.4(4) . . . 3_566 ?
Hg1 N22 C26 C25 57.7(6) . . . 3_566 ?
C27 N24 C26 N22 0.7(5) 2_556 . . . ?
C28 N24 C26 N22 177.7(5) . . . . ?
C27 N24 C26 C25 176.2(5) 2_556 . . 3_566 ?
C28 N24 C26 C25 -6.8(8) . . . 3_566 ?
Hg1 S2 C27 N23 4.7(5) . . . 2_546 ?
Hg1 S2 C27 N24 -176.3(4) . . . 2_546 ?
C27 N24 C28 C29 89.4(7) 2_556 . . . ?
C26 N24 C28 C29 -87.0(7) . . . . ?

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
C12 H12 S2 0.93 2.96 3.593(9) 126.8 4_675
C18 H18A N11 0.97 2.48 3.008(11) 114.0 .
C24 H24 S1 0.93 2.97 3.531(6) 120.1 .
C28 H28B N21 0.97 2.52 3.021(8) 112.1 3_566

_refine_diff_density_max         0.677
_refine_diff_density_min         -0.715
_refine_diff_density_rms         0.129

_shelxl_version_number           2013-3

